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

HRID 1749502ノート

反応式

HRID 1749502 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-0905cd3c69ee4e0fa96b06528047da41
出典データセット
uspto-grants-2015_10
特許番号
US09156798B2

反応ノート

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