Potassium Carbonate → N-Boc-cis-4-hydroxy-L-proline methyl ester

HRID 654157Notes

Reaction equation

HRID 654157 reaction equation
C([O:9][C@@H:10]1[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:12]([C:22]([O:24][CH3:25])=[O:23])[CH2:11]1)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO.C(OCC)(=O)C>[C:18]([O:17][C:15]([N:13]1[CH2:14][C@@H:10]([OH:9])[CH2:11][C@H:12]1[C:22]([O:24][CH3:25])=[O:23])=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 10760219(2S,4S)-1-tert-Butyl 2-methyl 4-(benzoyloxy)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 10752873N-Boc-cis-4-hydroxy-L-proline methyl esterYield 98.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,4S)-4-benzoyloxy-1-t-butoxycarbonyl-2-methoxycarbonylpyrrolidine (30.0 g) in methanol (600 ml) was added potassium carbonate (11.9 g) and the mixture was stirred at room temperature for 1 hour. The solution was diluted with ethyl acetate (1 l) and washed with water. The organic phase was washed with brine. The aqueous phase was saturated with sodium chloride, extracted with chloroform and washed with brine. The combined organic extracts were dried over magnesium sulfate and evaporated in vacuo to give an oil. The oil was chromatographed on a silica gel (500 g) column with a mixture of n-hexane and ethyl acetate (1:1) as an eluent to give (2S,4S)-1-t-butoxycarbonyl-4-hydroxy-2- methoxycarbonylpyrrolidine (20.7 g) as colorless crystal.

Workup

  1. washwashed with water
  2. washThe organic phase was washed with brine
  3. extractionextracted with chloroform
  4. washwashed with brine
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. customevaporated in vacuo
  7. customto give an oil
  8. customThe oil was chromatographed on a silica gel (500 g) column with a mixture of n-hexane and ethyl acetate (1:1) as an eluent

Sources & evidence

ORD record
ord-489845cdbe6847f2a1e6ac0dc6472362
Source dataset
uspto-grants-1992_07
Patent number
US05130323

Reaction notes

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