Methanol → HCID 178454083, compound

HRID 1257724Notes

Reaction equation

HRID 1257724 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11](SC)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].O[O:18][S:19]([O-:21])=O.[K+].[CH3:23]O>O.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:16])[NH:7][C@H:8]1[CH2:9][CH2:10][C@H:11]([S:19]([CH3:23])(=[O:21])=[O:18])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 178503847HCID 178503847, compound

Product 1

HCID 178454083HCID 178454083, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of trans (4-methylsulfanyl-cyclohexyl)-carbamic acid tert-butyl ester (0.51 g, 2.10 mmol) in methanol (7 mL) was cooled to 0° C. and treated with a suspension of oxone (1.28 g, 4.20 mmol) in water (3.1 mL). The mixture was stirred at ambient temperature for 20 minutes, then diluted with ethyl acetate and water. The phases were separated and the aqueous phase was extracted with ethyl acetate (×2). The combined organic extracts were washed with 10% aqueous citric acid solution, saturated sodium hydrogen carbonate solution, and brine, dried with sodium sulphate and concentrated under vacuum to give 412 mg (71%) of trans (4-methanesulfonyl-cyclohexyl)-carbamic acid tert-butyl ester as a white solid which was used without further purification. 1H NMR (400 MHz, CDCl3) δ: 4.39 (br s, 1H), 3.43 (br s, 1H), 2.83 (s, 3H), 2.78 (m, 1H), 2.25 (m, 4H), 1.67 (m, 2H), 1.44 (s, 9H), 1.28-1.12 (m, 2H).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate (×2)
  3. washThe combined organic extracts were washed with 10% aqueous citric acid solution, saturated sodium hydrogen carbonate solution, and brine
  4. dry with materialdried with sodium sulphate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7bdd4aead25f48a5b2d30d6d019baae0
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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