Benzyl (3-hydroxycyclohexyl)carbamate → Benzyl (3-oxocyclohexyl)carbamate

HRID 1013813ノート

反応式

HRID 1013813 の反応式
[CH2:1]([O:8][C:9](=[O:18])[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([OH:17])[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>ClCCl>[CH2:1]([O:8][C:9](=[O:18])[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 14476840Benzyl (3-hydroxycyclohexyl)carbamateHCID 178418287HCID 178418287、化合物

生成物 1

HCID 10171453Benzyl (3-oxocyclohexyl)carbamate収率 82%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Treat a solution of (3-hydroxy-cyclohexyl)-carbamic acid benzyl ester (15.5 g, 62.24) in dichloromethane (300 mL) with PCC (16.73 g, 77.81 mmol) and stir the mixture at room temperature for 12 hours. Filter the reaction mixture through celite. Remove the solvent in vacuo. Purify the residue on silica gel column using 25% to 50% ethyl acetate in hexanes gradient to afford 12.6 g (82%) of the title compound. MS (m/z): 248 (M+).

後処理

  1. filtrationFilter the reaction mixture through celite
  2. customRemove the solvent in vacuo
  3. customPurify the residue on silica gel column

出典と根拠

ORDレコード
ord-465aeaafce25464da4ee1600c86b5d31
出典データセット
uspto-grants-2011_07
特許番号
US07981918B2

反応ノート

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