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

HRID 1013813노트

반응식

HRID 1013813 반응식
[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

참가 물질

4

반응물 2

HCID 14476840Benzyl (3-hydroxycyclohexyl)carbamateHCID 178418287HCID 178418287, 화합물

생성물 1

HCID 10171453Benzyl (3-oxocyclohexyl)carbamate수율 82%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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+).

후처리

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

출처 및 근거

ORD 기록
ord-465aeaafce25464da4ee1600c86b5d31
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981918B2

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