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

HRID 1098775

反応式

HRID 1098775 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2b43d01dd3054975bff97961cfaa410d
出典データセット
uspto-grants-2012_03
特許番号
US08143290B2

関連ノート

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