反应 #1244305

反应方程式

ethyl (2R)-(3-chloro-2-hydroxypropyl)(1,1-diethoxyethyl)phosphinate

ammonia

→

ethyl (2S)-(3-amino-2-hydroxypropyl)(1,1-diethoxyethyl)phosphinate

收率 26.0%

溶剂

ethanol

反应条件

后处理

1. 1
   其他The solution was evaporated
2. 2
   其他the residue was purified by chromatography on a wet-packed silica gel column
3. 3
   洗涤eluting with methylene chloride/methanol (5-8% MeOH)
4. 4
   workup.ADDITIONcontaining 5% triethylamine
5. 5
   其他evaporated
6. 6
   workup.ADDITIONdiluted with methylene chloride and water
7. 7
   workup.ADDITIONThe aqueous layer was pH adjusted by the addition of a few mL of 10% aqueous Na2CO3
8. 8
   萃取repeatedly extracted with methylene chloride
9. 9
   干燥The combined organic layers were dried over Na2SO4
10. 10
    其他evaporated

实验过程

A solution of ethyl (2R)-(3-chloro-2-hydroxypropyl)(1,1-diethoxyethyl)phosphinate (5.0 g, 17 mmol) in ethanol containing 9% of ammonia was stirred in an autoclave at room temperature for 4 days and at 60° C. for one further day. The solution was evaporated and the residue was purified by chromatography on a wet-packed silica gel column eluting with methylene chloride/methanol (5-8% MeOH) containing 5% triethylamine. The appropriate fractions were combined, evaporated and diluted with methylene chloride and water. The aqueous layer was pH adjusted by the addition of a few mL of 10% aqueous Na2CO3 and repeatedly extracted with methylene chloride. The combined organic layers were dried over Na2SO4 and evaporated to give 1.2 g (26%) of ethyl (2S)-(3-amino-2-hydroxypropyl)(1,1-diethoxyethyl)phosphinate as a clear oil. Data: 1H NMR (300 MHz, CDCl3) δ 4.40-4.55 (b, 1H), 4.10-4.30 (m, 2H), 3.55-3.80 (m, 4H), 3.20-3.30 (m, 1H), 3.00-3.10 (m, 1H), 2.00-2.40 (m, 2H), 1.45-1.53 (dd, J=3.4, 11.7 Hz, 3H), 1.30-1.40 (m, 3H), 1.15-1.25 (m, 6H).

来源