Dimethyl Sulfoxide → Benzyl [(1r,2r)-2-formylcyclohexyl]carbamate

HRID 1592336ノート

反応式

HRID 1592336 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:18][C:19](=[O:29])[NH:20][C@@H:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]1[CH2:27][OH:28])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[CH2:11]([O:18][C:19](=[O:29])[NH:20][C@@H:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]1[CH:27]=[O:28])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 24720936Benzyl trans-(2-hydroxymethyl)cyclohexylcarbamate

生成物 1

HCID 29923903Benzyl [(1r,2r)-2-formylcyclohexyl]carbamate収率 97%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

A solution of oxalyl chloride (2.6 mL, 29.4 mmol) in dichloromethane (80 mL) at −78° C. was treated with a solution of dimethyl sulfoxide (4.3 mL, 60.8 mmol) in dichloromethane (10 mL) over 5 minutes. The mixture was stirred for 40 min, then treated with a solution of benzyl[(1R,2R)-2-(hydroxymethyl)cyclohexyl]carbamate (5.0 g, 19 mmol) in dichloromethane (20 mL) over 5 minutes. The mixture was stirred for 45 minutes, then was treated with triethylamine (8.6 mL, 61.7 mmol) and allowed to warm to room temperature. After 60 minutes, the mixture was washed with water, then with brine, and dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography using 30% ethyl acetate in hexane to provide a white solid (4.8 g, 97%).

後処理

  1. stirringThe mixture was stirred for 45 minutes
  2. waitAfter 60 minutes
  3. washthe mixture was washed with water
  4. dry with materialwith brine, and dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography

出典と根拠

ORDレコード
ord-2ab0c87a156d407985ea7433715f7980
出典データセット
uspto-grants-2007_11
特許番号
US07291744B2

反応ノート

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