Hydrochloric Acid → 1-Cbz-2-methylpyrrolidine-2-carboxylic Acid

HRID 415268Notes

Reaction equation

HRID 415268 reaction equation
[CH3:1][C:2]1([C:17]([O:19]C)=[O:18])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].CO.O.[OH-].[Li+].Cl>O>[CH2:10]([O:9][C:7]([N:3]1[CH2:4][CH2:5][CH2:6][C:2]1([CH3:1])[C:17]([OH:19])=[O:18])=[O:8])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 25194662HCID 25194662, compound

Product 1

HCID 202354571-Cbz-2-methylpyrrolidine-2-carboxylic AcidYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

To the solution of 1-benzyl 2-methyl 2-methylpyrrolidine-1,2-dicarboxylate (3.1 g, 10.8 mmol) in the mixture of Methanol (20 mL) and water (20 mL) was added lithium hydroxide monohydrate (0.9 g, 21.6 mmol). The mixture was stirred at 30° C. for 3 h. The resulting mixture was treated with 5N hydrochloric acid to pH=2 and filtrated, washed with water, dried in vacuum at 45° C. 1.9 g of 1-(benzyloxycarbonyl)-2-methylpyrrolidine-2-carboxylic acid was obtained. Yield: 67%. LC-MS (ESI) m/z: 264 (M+1)+.

Workup

  1. filtrationfiltrated
  2. washwashed with water
  3. customdried in vacuum at 45° C

Sources & evidence

ORD record
ord-5e0abb10d45d4c4a8120f5043fb18b4c
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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