Isopropanol → tert-Butyl ((1R,2S)-1-hydroxy-1-(3-methoxyphenyl)propan-2-yl)carbamate

HRID 1098775

Reaction equation

HRID 1098775 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9](=[O:20])[C@@H:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:11])[CH:6]=[CH:7][CH:8]=1.CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].CC(O)C>C1(C)C=CC=CC=1>[OH:20][C@H:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[C@@H:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:16])[CH3:17])[CH3:11]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 11143Aluminum isopropoxideHCID 59339682tert-Butyl [(1S)-2-(3-methoxyphenyl)-1-methyl-2-oxoethyl]carbamate

Product 1

HCID 59339845tert-Butyl ((1R,2S)-1-hydroxy-1-(3-methoxyphenyl)propan-2-yl)carbamateYield 98.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of tert-butyl [(1S)-2-(3-methoxyphenyl)-1-methyl-2-oxoethyl]carbamate (13.6 g, 48.7 mmol), aluminum isopropoxide (1.99 g, 9.70 mmol), 2-propanol (41 mL, 535 mmol) in toluene (63 mL) was stirred under an atmosphere of argon at 50° C. overnight. LC/MS showed complete conversion into the alcohol. The mixture was partitioned between ethyl acetate (200 mL) and hydrochloric acid (1M, 200 mL). The organic phase was washed with water (200 mL), dried over magnesium sulfate and concentrated to give the subtitle compound as a syrup (13.5 g). The compound was used in the next step without further purification.

Workup

  1. customThe mixture was partitioned between ethyl acetate (200 mL) and hydrochloric acid (1M, 200 mL)
  2. washThe organic phase was washed with water (200 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2b43d01dd3054975bff97961cfaa410d
Source dataset
uspto-grants-2012_03
Patent number
US08143290B2

Linked notes

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