Methanol → HCID 178501147, compound

HRID 1893334Notes

Reaction equation

HRID 1893334 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11](O)=[O:12])[CH2:7][CH2:6]1)=[O:4].CO>O1CCCC1>[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][OH:12])[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 887MethanolHCID 178501163HCID 178501163, compound

Product 1

HCID 178501147HCID 178501147, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid (10.0 g, 53.7 mmol) in tetrahydrofuran (540 ml) was added borane-dimethylsulfide complex (6.80 g, 80.6 mmol) at 0-5° C. The cooling bath was removed after 15 minutes and the mixture was stirred for 4 h. The reaction mixture was quenched with methanol (17.2 g, 537 mmol), stirred for 20 minutes and concentrated in vacuo. The residue was triturated in tert-butyl methyl ether (300 ml) and filtrated over a pad of Decalite. The filtrate was concentrated in vacuo. The residue was partitioned between ethyl acetate (300 ml) and 1 M aqueous sodium hydroxide solution (100 ml). The layers were separated. The organic layer was washed with one 100 ml-portion of water. The combined aqueous layers were extracted with one 150-ml portion of ethyl acetate. The combined organic layers were washed with one 50 ml-portion of brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound (8.75 g, 94.6%) as colorless oil, which can be used without further purification. MS m/e: 172 (M+)

Workup

  1. customThe cooling bath was removed after 15 minutes
  2. stirringstirred for 20 minutes
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated in tert-butyl methyl ether (300 ml)
  5. filtrationfiltrated over a pad of Decalite
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe residue was partitioned between ethyl acetate (300 ml) and 1 M aqueous sodium hydroxide solution (100 ml)
  8. customThe layers were separated
  9. washThe organic layer was washed with one 100 ml-portion of water
  10. extractionThe combined aqueous layers were extracted with one 150-ml portion of ethyl acetate
  11. washThe combined organic layers were washed with one 50 ml-portion of brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7cd704216cfa4f6390a6514467f07955
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

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