Water → (S)-tert-Butyl (1-hydroxy-3-methylbutan-2-yl)(methyl)carbamate
Reaction equation
[C:1]([N:8]([CH3:16])[C@H:9]([C:13](O)=[O:14])[CH:10]([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].B.C1COCC1.O.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[C:4]([O:3][C:1](=[O:2])[N:8]([C@H:9]([CH2:13][OH:14])[CH:10]([CH3:11])[CH3:12])[CH3:16])([CH3:5])([CH3:7])[CH3:6]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
20.0 g Boc-MeVal-OH (86.5 mmol; Fluka) were dissolved in 80 ml THF and cooled to 0° C. 130 ml 1M BH3-THF (0.13 mol; Fluka) were added at 0° C. over 1 h and the clear, colo reaction mixture was warmed up and stirred at RT for 1 h. The reaction mixture was again cooled to 0° C., 75 ml deionized water were carefully added at 0-5° C. over 0.5 h and after warming up to RT stirring was continued for 1 h. To the colorless solution were added 150 ml 10% Na2CO3 all at once and after stirring for 1 h the reaction mixture was extracted with 600 ml and 300 ml ethyl acetate. The organic layers were washed with brine and dried (Na2SO4). Removal of the solvent by rotary evaporation gave 17.4 g (94%) product as colorless oil. 1H-NMR:
Workup
- customthe clear, colo reaction mixture
- temperaturewas warmed up
- temperatureThe reaction mixture was again cooled to 0° C.
- additionwere carefully added at 0-5° C. over 0.5 h
- temperatureafter warming up to RT
- stirringstirring
- waitwas continued for 1 h
- stirringafter stirring for 1 h the reaction mixture
- extractionwas extracted with 600 ml and 300 ml ethyl acetate
- washThe organic layers were washed with brine
- dry with materialdried (Na2SO4)
- customRemoval of the solvent
- customby rotary evaporation
Sources & evidence
- ORD record
- ord-859cec6dd58c434a95af38e53a7d858b
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07312343B2
Reaction notes
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