Lithium Hydroxide → (4S)-1-BOC-4-[acetyl(4,4-dimethylcyclohexyl)amino]-L-proline

HRID 884036Notes

Reaction equation

HRID 884036 reaction equation
[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([C:22](=[O:24])[CH3:23])[CH:14]2[CH2:19][CH2:18][C:17]([CH3:21])([CH3:20])[CH2:16][CH2:15]2)[CH2:10][C@H:9]1[C:25]([O:27]C)=[O:26])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Li+].[OH-]>CO.O>[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([C:22](=[O:24])[CH3:23])[CH:14]2[CH2:19][CH2:18][C:17]([CH3:21])([CH3:20])[CH2:16][CH2:15]2)[CH2:10][C@H:9]1[C:25]([OH:27])=[O:26])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67359765Methyl(2S,4S)-1-BOC-4-[acetyl(4,4-dimethylcyclohexyl)amino]pyrrolidine-2-carboxylate

Product 1

HCID 67357391(4S)-1-BOC-4-[acetyl(4,4-dimethylcyclohexyl)amino]-L-prolineYield 97.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl (2S,4S)-1-BOC-4-[acetyl(4,4-dimethylcyclohexyl)amino]pyrrolidine-2-carboxylate (0.98 g, 2.47 mmol) obtained in Step B, was dissolved in MeOH (8 mL) and water (1.6 mL). LiOH (0.18 g, 7.52 mmol) was added thereto at 0˜5° C. After the reaction mixture was stirred at room temperature for 3 hours and concentrated in vacuo, the obtained residue was diluted with water and the solution was extracted with EtOAc. The extracted organic solution was washed with brine, dried over MgSO4, and concentrated in vacuo to give the title compound (0.92 g, 97%).

Workup

  1. customat 0˜5° C
  2. concentrationconcentrated in vacuo
  3. additionthe obtained residue was diluted with water
  4. extractionthe solution was extracted with EtOAc
  5. washThe extracted organic solution was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4cc2e667eaea4ac5b501ef8d722a7a38
Source dataset
uspto-grants-2012_08
Patent number
US08236955B2

Reaction notes

Loading…