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

HRID 1666016Notes

Reaction equation

HRID 1666016 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-e7f560dd563a46ccaa5261d8b05273fb
Source dataset
uspto-grants-2011_10
Patent number
US08039622B2

Reaction notes

Loading…