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

HRID 1098775

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HRID 1098775 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2b43d01dd3054975bff97961cfaa410d
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143290B2

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