4-Methylmorpholine → (R)-tert-Butyl 1-ethoxy-3-hydroxypropan-2-ylcarbamate
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][O:14][CH2:15][CH3:16])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OCC(C)C)=O.CN1CCOCC1.[BH4-].[Na+]>C1COCC1.O.CCOC(C)=O>[CH2:15]([O:14][CH2:13][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:10][OH:11])[CH3:16]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -15 °C
Procedure
To a solution of (S)-2-(tert-butoxycarbonylamino)-3-ethoxypropanoic acid (1.81 g, 7.76 mmol) in THF (20 mL) at −15° C. was added isobutyl chloroformate (1.015 mL, 7.76 mmol) in THF (5 mL) and 4-methylmorpholine (0.853 mL, 7.76 mmol) in THF (5 mL). After stirring for 10 min at −15° C., the mixture was slowly added to a solution of sodium borohydride (0.881 g, 23.28 mmol) in H2O (7 mL). The mixture was stirred at −15° C. for 30 min and was diluted with EtOAc. The organic layer was washed with saturated aq NaHCO3 and brine and dried. The residue was carried to next step without further purification (1.6 g, 94%). [M+H] calc'd for C10H21NO4, 220. found, 220.
Workup
- stirringThe mixture was stirred at −15° C. for 30 min
- washThe organic layer was washed with saturated aq NaHCO3 and brine
- customdried
- customThe residue was carried to next step without further purification (1.6 g, 94%)
Sources & evidence
- ORD record
- ord-8461a68741044a89a7cb68cb2d38e68f
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08440689B2
Reaction notes
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