Tetrabutylammonium Fluoride → benzyl N-(4-hydroxy-1-methylcyclohexyl)carbamate

HRID 475380Notes

Reaction equation

HRID 475380 reaction equation
[CH2:1]([O:8][C:9](=[O:26])[NH:10][C:11]1([CH3:25])[CH2:16][CH2:15][CH:14]([O:17][Si](C(C)(C)C)(C)C)[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([O:8][C:9](=[O:26])[NH:10][C:11]1([CH3:25])[CH2:12][CH2:13][CH:14]([OH:17])[CH2:15][CH2:16]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66756916(4-(Tert-butyl-dimethyl-silanyloxy)-1-methyl-cyclohexyl)-carbamic acid benzyl ester

Product 1

HCID 66756996benzyl N-(4-hydroxy-1-methylcyclohexyl)carbamateYield 77.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of example 45D (341 mg, 0.91 mmol) in tetrahydrofuran (5 mL) was added tetrabutylammonium fluoride (1 M solution in THF, 2.0 mL, 2 mmol). The resulting brown solution was stirred at room temperature for 24 hours and then concentrated in vacuo and partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer was dried over sodium sulfate, filtered and concentrated to afford a crude oil. The crude oil was purified by flash chromatography using a linear gradient of 80% hexane/20% ethyl acetate to 80% ethyl acetate/20% hexane to give the title compound (185 mg) as an inseparable mixture of diastereomers. MS (CI) m/z 264 (M+1)+.

Workup

  1. concentrationconcentrated in vacuo
  2. custompartitioned between ethyl acetate (100 mL) and water (100 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a crude oil
  7. customThe crude oil was purified by flash chromatography

Sources & evidence

ORD record
ord-511eae7cb2a54fe2a09de35bd629b953
Source dataset
uspto-grants-2014_01
Patent number
US08637546B2

Reaction notes

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