2-{[(Tert-butoxy)carbonyl](methyl)amino}-2-methylpropanoic acid → tert-butyl N-(1-hydroxy-2-methylpropan-2-yl)-N-methylcarbamate
Reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:15])[C:9]([CH3:14])([C:11](O)=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[OH:12][CH2:11][C:9]([N:8]([CH3:15])[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:10])[CH3:14]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
A solution of N-(tert-butoxycarbonyl)-N,2-dimethylalanine in THF (0.17 M) was treated at RT with BH3-DMS complex in THF (10 eq., 2M) and the mixture was stirred at 45° C. for 8 h. The reaction was carefully quenched with H2O and the pH adjusted to 9 with 2M aq. Na2CO3. The mixture was then extracted with EtOAc and washed with brine. After drying over Na2SO4, the crude material was purified by FC (10-50% EtOAc in PE) to afford the product. (ES+) m/z 204 (M+H)+.
Workup
- customThe reaction was carefully quenched with H2O
- extractionThe mixture was then extracted with EtOAc
- washwashed with brine
- dry with materialAfter drying over Na2SO4
- customthe crude material was purified by FC (10-50% EtOAc in PE)
- customto afford the product
Sources & evidence
- ORD record
- ord-2532df387ca344f4a428e9d6f2f5219a
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07989438B2
Reaction notes
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