Methanol → [(3S)-3-Hydroxy-3-(2-thiazolyl)propyl]carbamic acid 1,1-dimethylethyl ester

HRID 966962

Reaction equation

B.O1CCCC1.[CH3:7][C:8]([O:11][C:12](=[O:23])[NH:13][CH2:14][CH2:15][C:16](=[O:22])[C:17]1[S:18][CH:19]=[CH:20][N:21]=1)([CH3:10])[CH3:9].CO.C(OCC)(=O)C>O1CCCC1.CCCC(C)C>[CH3:10][C:8]([O:11][C:12](=[O:23])[NH:13][CH2:14][CH2:15][C@H:16]([OH:22])[C:17]1[S:18][CH:19]=[CH:20][N:21]=1)([CH3:7])[CH3:9]

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of (R)-3-methyl-CBS-oxazaborolidine (1M solution in toluene, 0.43 ml) in dry tetrahydrofuran (30 ml) at −10° C. under nitrogen, was added borane-tetrahydrofuran complex (1M in tetrahydrofuran, 2.58 ml) and the mixture was stirred at −10° C. for 15 minutes. A solution of [3-oxo-3-(2-thiazolyl)propyl]carbamic acid 1,1-dimethylethyl ester (1.1 g, 4.3 mmol) in dry tetrahydrofuran (20 ml) was added dropwise over 45 minutes and the resulting mixture was allowed to warm up to room temperature over 16 h. Methanol (10 ml) was added and the mixture was stirred at room temperature for 15 minutes before the solvent was removed at reduced pressure. Methanol (10 ml) was again added and removed at reduced pressure to leave a crude yellow oil. Flash chromatography (silica, 25 to 100% ethyl acetate in isohexane) afforded a clear gum (0.74 g, 67%).

Workup

temperatureto warm up to room temperature over 16 h
stirringthe mixture was stirred at room temperature for 15 minutes before the solvent
customwas removed at reduced pressure
additionMethanol (10 ml) was again added
customremoved at reduced pressure
customto leave a crude yellow oil

Sources & evidence

ORD record: ord-9ffbe8647db3472f8a14c94b80cf27c2
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06953797B2

Linked notes

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