Lithium Hydroxide → tert-butyl ((1S,2R)-2-hydroxycyclohexyl)carbaMate

HRID 539079Notes

Reaction equation

HRID 539079 reaction equation
[N+](C1C=CC(C([O:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]2[NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=O)=CC=1)([O-])=O.[Li+].[OH-]>C1COCC1>[OH:10][C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]1[NH:17][C:18](=[O:19])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68089026(1R,2S)-2-(tert-butoxycarbonylamino)cyclohexyl 4-nitrobenzoate

Product 1

HCID 11333385tert-butyl ((1S,2R)-2-hydroxycyclohexyl)carbaMateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (1R,2S)-2-(tert-butoxycarbonylamino)cyclohexyl 4-nitrobenzoate (1.95 g, 5.35 mmol) in THF (50 mL) was added a solution of 1N LiOH (9.63 mL, 9.63 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 6 hours and then partitioned between EtOAc and water. The organic layer was washed with brine, dried and concentrated. The residue was purified by column chromatography (EtOAc/hexane, 1:1) to give tert-butyl (1S,2R)-2-hydroxycyclohexylcarbamate (1.15 g, 100%).

Workup

  1. custompartitioned between EtOAc and water
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (EtOAc/hexane, 1:1)

Sources & evidence

ORD record
ord-0986cb45edca459e88d5ca9d1244cd01
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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