Tetrahydrofuran → cis-4-(Boc-amino)-1-methylcyclohexanol

HRID 2270105Notes

Reaction equation

HRID 2270105 reaction equation
O1CCC[CH2:2]1.[O:6]=[C:7]1[CH2:12][CH2:11][CH:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:9][CH2:8]1.C[Li]>O>[OH:6][C:7]1([CH3:2])[CH2:8][CH2:9][CH:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamateHCID 178418348HCID 178418348, compound

Product 1

HCID 21877240cis-4-(Boc-amino)-1-methylcyclohexanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 6 ml anhydrous tetrahydrofuran solution of 303 mg (1.42 mmol) of tert-butyl N-(4-oxocyclohexyl)carbamate, 2.7 ml of methyl lithium (1.1M in hexane, 2.98 mmol) was dropwise added at −78° C. under an argon atmosphere and stirred for 1.5 hours, after adding 20 ml of water thereto to return room temperature, followed by extracting with 30 ml of methylene chloride after drying over anhydrous sodium sulfate, the solvent was distilled off and the residue was purified by a silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain 150 mg (46%) of non-polar side diastereomer as a colorless crystal and 54 mg (17%) of polar side diastereomer as a colorless crystal.

Workup

  1. customto return room temperature
  2. extractionby extracting with 30 ml of methylene chloride
  3. dry with materialafter drying over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off
  5. customthe residue was purified by a silica gel column chromatography (hexane/ethyl acetate=1/1)
  6. customto obtain 150 mg (46%) of non-polar side diastereomer as a colorless crystal and 54 mg (17%) of polar side diastereomer as a colorless crystal

Sources & evidence

ORD record
ord-fc6be517bee244c69d4966e2e9eee1be
Source dataset
uspto-grants-2001_12
Patent number
US06331548B1

Reaction notes

Loading…