Tetrahydrofuran → tert-butyl 3(S)-[N-benzyl-N-(alpha(S)-methylbenzyl)amino]-2(S)-hydroxyheptanoate

Temperature

0 °C

A solution of 0.66 ml of (S)-(−)-N-benzyl-α-methylbenzylamine in 10 ml of tetrahydrofuran was cooled to 0° C. and 1.88 ml of a 1.6M solution of n-butyllithium in hexane were added dropwise via a syringe. The resulting dark pink solution was stirred at 0° C. for 45 minutes and then cooled to −78° C. A solution of 0.184 g of tert-butyl (E)-2-heptenoate in 2 ml of anhydrous diethyl ether was added and the mixture was stirred for 2 hours at −78° C. 0.37 g of solid (1S)-(+)-(10-camphorsulphonyl)oxaziridine was added and the mixture was stirred at −78° C. for 1 hour. The mixture was warmed to 0° C. and a saturated ammonium chloride solution was added. The tetrahydrofuran was evaporated and the aqueous phase was diluted with water and extracted with dichloromethane. The organic phase was dried over magnesium sulphate, evaporated and purified by chromatography on silica gel using a 10% solution of diethyl ether in hexane for the elution to give 0.35 g of tert-butyl 3(S)-[N-benzyl-N-(α(S)-methylbenzyl)amino]-2(S)-hydroxyheptanoate as a colorless oil, MS: m/e 412.2 [M+H]+.

1. temperaturecooled to −78° C
2. stirringthe mixture was stirred for 2 hours at −78° C
3. stirringthe mixture was stirred at −78° C. for 1 hour
4. temperatureThe mixture was warmed to 0° C.
5. customThe tetrahydrofuran was evaporated
6. additionthe aqueous phase was diluted with water
7. extractionextracted with dichloromethane
8. dry with materialThe organic phase was dried over magnesium sulphate
9. customevaporated
10. custompurified by chromatography on silica gel using a 10% solution of diethyl ether in hexane
11. washfor the elution

ORD record

ord-9aa01dd7d0e542f9b50491b1d3a049d4

Source dataset

uspto-grants-2001_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06187905B1