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

HRID 1749502Notes

Reaction equation

HRID 1749502 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-0905cd3c69ee4e0fa96b06528047da41
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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