4-Methylmorpholine → tert-butyl ((2R,3R)-1-hydroxy-3-methoxybutan-2-yl)carbamate

To a cold solution (−15° C.) of BocThr(Me)OH (5.14 g, 22 mmol) in dichloroethane (22 mL) were successively added N-methyl morpholine (2.44 mL, 22 mmol) and isobutyl chloroformate (2.99 mL, 22 mmol). After one min, the precipitate was filtered and washed with dichloroethane (5×4 mL). The filtrate and washings were combined in a large three neck flask in an ice-salt bath. A solution of NaBH4 (1.26 g, 33 mmol) in H2O (11 mL) was added at once, proceeding a strong evolution of gas, followed by H2O (500 mL). The mixture was then extracted with EtOAc (5×150 mL). The combined EtOAc was dried (Na2SO4) and concentrated to give the titled compound (5 g). MS (MH+ 220).

1. filtrationthe precipitate was filtered
2. washwashed with dichloroethane (5×4 mL)
3. customThe filtrate and washings were combined in a large three neck flask in an ice-salt bath
4. extractionThe mixture was then extracted with EtOAc (5×150 mL)
5. dry with materialThe combined EtOAc was dried (Na2SO4)
6. concentrationconcentrated

ORDレコード

ord-9ece6fafd7ff45a581063177c7130666

出典データセット

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08426414B2