HCID 45119438, compound → Methyl methyl(3-oxocyclohexyl)carbamate

HRID 42978Notes

Reaction equation

HRID 42978 reaction equation
[CH3:1][O:2][C:3](=[O:13])[N:4]([CH3:12])[C:5]1[CH2:10][CH2:9][CH2:8][C:7](=[O:11])[CH:6]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:13])[N:4]([CH3:12])[CH:5]1[CH2:10][CH2:9][CH2:8][C:7](=[O:11])[CH2:6]1

Participants

4

Reactant 1

HCID 45119438HCID 45119438, compound

Product 1

HCID 45119437Methyl methyl(3-oxocyclohexyl)carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl-(3-oxo-cyclohex-1-enyl)-carbamic acid methyl ester (412 mg, 2.2 mmol) in methanol (20 ml) is hydrogenated with Pd/C (10%, 80 mg, 1 bar). After filtration the crude product is chromatographed on silica gel (30 g) with hexane/ethyl acetate (1:1 v/v) as eluent. Methyl-(3-oxo-cyclohexyl)-carbamic acid methyl ester is obtained as a colorless oil. NMR (400 MHz; CDCl3): 4.23 (br, 1H), 3.69 (s, 3H), 2.83 (br,s, 3H), 2.57-2.34 (m, 3H), 2.21 (td, J=14 Hz, J=6 Hz, 1H), 2.05 (m, 1H), 1.91 (m, 1H), 1.80 (qd, J=12.5 Hz, J=3.5 Hz, 1H), 1.6 (m, 1H).

Workup

  1. filtrationAfter filtration the crude product
  2. customis chromatographed on silica gel (30 g) with hexane/ethyl acetate (1:1 v/v) as eluent

Sources & evidence

ORD record
ord-eb06c7c0d5514132b7e1d3078dac1de3
Source dataset
uspto-grants-2013_09
Patent number
US08536229B2

Reaction notes

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