HCID 178418287, compound → tert-butyl N-(4-oxocyclohexyl)carbamate

HRID 246649Notes

Reaction equation

HRID 246649 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>ClCCl>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 178418287HCID 178418287, compoundHCID 178418329HCID 178418329, compound

Product 1

HCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamateYield 80.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl trans-4-hydroxycyclohexylcarbamate (2.0 g, 9.3 mmol) in 100 mL of dichloromethane was added PCC (3.0 g, 14 mmol) and celite (5.0 g). The reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered through a celite pad and the residue concentrated under reduced pressure. The crude compound was purified by column chromatography (silica gel, 200-300 mesh, eluting with a mixture of ethyl acetate and petroleum ether (1:1, v/v) to give tert-butyl 4-oxocyclohexylcarbamate (1.6 g, 80%) as a white solid. 1H NMR (300 MHz, CDCl3): δ 4.52 (brs, 1H), 3.94 (brs, 1H), 2.45-2.40 (m, 4H), 2.20-2.27 (m, 2H), 1.74-1.63 (m, 2H), 1.46 (s, 9H).

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. concentrationthe residue concentrated under reduced pressure
  3. customThe crude compound was purified by column chromatography (silica gel, 200-300 mesh
  4. washeluting with a mixture of ethyl acetate and petroleum ether (1:1

Sources & evidence

ORD record
ord-ea5be1a42b99436faee86c9ace84b420
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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