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Amination [Synthetic Reagents]
The Gabriel reagent is widely used as a nucleophilic aminating agent since its reactivity is reliable and its handling is easy.1) A variety of aminating agents analogous to the Gabriel reagent have been reported.
The potassium salt of imide 1 reacts with alkyl halide to give imide 2. 2 is treated with base or acid to give either N-Boc-amine 3 or N-methoxycarbonylamine 4, respectively. Moreover, 1 also serves as an acid nucleophile in the Mitsunobu reaction to allow for the conversion of hydroxy groups to amino groups. Therefore, 1 is a useful reagent to give monoprotected amines.2)
The potassium salt of imide 1 reacts with alkyl halide to give imide 2. 2 is treated with base or acid to give either N-Boc-amine 3 or N-methoxycarbonylamine 4, respectively. Moreover, 1 also serves as an acid nucleophile in the Mitsunobu reaction to allow for the conversion of hydroxy groups to amino groups. Therefore, 1 is a useful reagent to give monoprotected amines.2)
Fukuyama and co-workers have demonstrated various reactions using the N-substituted sulfonamide 5.3) Smooth reactions of 5 occur with alkyl halides under basic conditions and alcohols under Mitsunobu conditions to provide o-nitrobenzenesulfonyl (o-Ns) amines 6. The various o-Ns amines (Alloc, Boc, Cbz) 6 obtained from these reactions can be selectively deprotected, under the appropriate conditions, to afford the monoprotected amines 7 and 8. Furthermore, 7 can be converted to the primary amine in high yields via a second deprotection. 8 can be converted to the secondary amine in high yields by repeating the alkylation and deprotection process.4)
On the other hand, acetoxime O-(2,4,6-trimethylphenyl)sulfonate 9 has been reported as a useful electrophilic aminating agent. 9 reacts with Grignard reagents in the presence of a catalytic amount of magnesium chloride to afford primary amines in good yields.5)
References
- 1)a) S. Gabriel, Ber. 1887, 20, 2224.
- 2)a) J. D. Elliott, J. H. Jones, J. Chem. Soc., Chem. Commun. 1977, 758.
- 3)T. Fukuyama, M. Cheung, T. Kan, Synlett 1999, 1301.
- 4)T. Kan, A. Fujiwara, H. Kobayashi, T. Fukuyama, Tetrahedron 2002, 58, 6267.
- 5)E. Erdik, M. Ay, Synth. React. Inorg. Met.-Org. Chem. 1989, 19, 663.
| Product Number | A1137 |
| CAS RN | 584-13-4 |
| Purity / Analysis Method: | >98.0%(T)(HPLC) |
| Product Number | A1441 |
| CAS RN | 81549-07-7 |
| Purity / Analysis Method: | >98.0%(HPLC) |
| Product Number | B1648 |
| CAS RN | 18303-04-3 |
| Purity / Analysis Method: | >98.0%(T)(HPLC) |
| Product Number | B1734 |
| CAS RN | 85232-02-6 |
| Purity / Analysis Method: | >98.0%(N) |
| Product Number | B2303 |
| CAS RN | 198572-71-3 |
| Purity / Analysis Method: | >98.0%(T)(HPLC) |
| Product Number | B5402 |
| CAS RN | 148017-28-1 |
| Purity / Analysis Method: | >98.0%(T)(N) |
| Product Number | C1757 |
| CAS RN | 245365-64-4 |
| Purity / Analysis Method: | >98.0%(T)(HPLC) |
| Product Number | I0510 |
| CAS RN | 66389-76-2 |
| Purity / Analysis Method: | >98.0%(GC) |
| Product Number | P0403 |
| CAS RN | 1074-82-4 |
| Purity / Analysis Method: | >98.0%(T) |
| Product Number | P1235 |
| CAS RN | 119812-51-0 |
| Purity / Analysis Method: | >98.0%(T) |
| Product Number | P2856 |
| CAS RN | 1293990-73-4 |
| Purity / Analysis Method: | >98.0%(T) |
| Product Number | D2479 |
| CAS RN | 18197-26-7 |
| Purity / Analysis Method: | >97.0%(T)(N) |
Product Number: A1137 |
Purity / Analysis Method:
>98.0%(T)(HPLC)
Product Number: A1441 |
Purity / Analysis Method:
>98.0%(HPLC)
Product Number: B1648 |
Purity / Analysis Method:
>98.0%(T)(HPLC)
Product Number: B1734 |
Purity / Analysis Method:
>98.0%(N)
Product Number: B2303 |
Purity / Analysis Method:
>98.0%(T)(HPLC)
Product Number: B5402 |
Purity / Analysis Method:
>98.0%(T)(N)
Product Number: C1757 |
Purity / Analysis Method:
>98.0%(T)(HPLC)
Product Number: I0510 |
Purity / Analysis Method:
>98.0%(GC)
Product Number: P0403 |
Purity / Analysis Method:
>98.0%(T)
Product Number: P2856 |
Purity / Analysis Method:
>98.0%(T)
Product Number: D2479 |
Purity / Analysis Method:
>97.0%(T)(N)
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