Water → HCID 59021631, compound
Reaction equation
[C:1]([N:8]([CH3:17])[C@H:9]([C:14](O)=[O:15])[C@H:10]([CH2:12][CH3:13])[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]([CH2:14][OH:15])[C@@H:10]([CH3:11])[CH2:12][CH3:13])[CH3:17])([CH3:5])([CH3:7])[CH3:6]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
39.3 g Boc-MeIle-OH (0.160 mol; Synthetech) were dissolved in 160 ml THF and cooled to 0° C. 240 ml 1M BH3-THF (0.24 mol; Fluka) were added at 0° C. over 1 h and the clear, colorless reaction mixture was warmed up and stirred at RT for 1 h. The reaction mixture was again cooled to 0° C., 100 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 250 ml 10% Na2CO3 all at once and after stirring for 1 h the reaction mixture was extracted with 1000 ml and 500 ml ethyl acetate. The organic layers were washed with brine and dried (Na2SO4). Removal of the solvent by rotary evaporation gave 36.9 g (99.7%) product as colorless oil.
Workup
- temperaturethe clear, colorless reaction mixture was 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 1000 ml and 500 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-94b2753d6a384b5983e4c50ef8a255d8
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07312343B2
Reaction notes
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