Triacetoxyperiodinane → (3-Oxo-cyclohexyl)-carbamic acid tert-butyl ester

HRID 1749502노트

반응식

HRID 1749502 반응식
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:11]([O:10][C:9](=[O:15])[NH:8][CH:4]1[CH2:5][CH2:6][CH2:7][C:2](=[O:1])[CH2:3]1)([CH3:14])([CH3:12])[CH3:13]

참가 물질

4

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 21925254tert-Butyl (3-hydroxycyclohexyl)carbamate

생성물 1

HCID 44228975(3-Oxo-cyclohexyl)-carbamic acid tert-butyl ester수율 91.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of tert-butyl (3-hydroxycyclohexyl)carbamate (4.40 g, 20.46 mmol) in DCM (250 mL) was added Dess-Martin periodinane (13.0 g, 30.70 mmol) in portions under cooling in an ice bath. The mixture was stirred at room temperature for 2 h. The reaction was diluted with DCM and washed with aqueous sodium carbonate. The separated organic layer was dried over anhydrous sodium sulfate and concentrated. The crude compound was purified by silica gel column chromatography (40% ethyl acetate in petroleum ether) to afford the title compound (4.0 g, 18.78 mmol, 91% yield). MS (ESI) m/z 214.1 [M+H]+.

후처리

  1. temperatureunder cooling in an ice bath
  2. washwashed with aqueous sodium carbonate
  3. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe crude compound was purified by silica gel column chromatography (40% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-0905cd3c69ee4e0fa96b06528047da41
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156798B2

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