Sodium Hydroxide → DL-Proline, 1-[(3-fluorophenyl)methyl]-5-oxo-

HRID 1252287Notes

Reaction equation

HRID 1252287 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH2:10][N:11]2[CH:15]([C:16]([O:18]C)=[O:17])[CH2:14][CH2:13][C:12]2=[O:20])[CH:7]=[CH:8][CH:9]=1>O>[F:3][C:4]1[CH:5]=[C:6]([CH2:10][N:11]2[C:12](=[O:20])[CH2:13][CH2:14][CH:15]2[C:16]([OH:18])=[O:17])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13885244HCID 13885244, compound

Product 1

HCID 4125295DL-Proline, 1-[(3-fluorophenyl)methyl]-5-oxo-Yield 66.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 19.00 g of sodium hydroxide pellets in 225 ml of water was treated with 115.52 g of (±)-1-[(3-fluorophenyl)methyl]-5-methoxycarbonyl-2-pyrrolidinone and the mixture was heated for four hours (steam bath). The solution was cooled to the ambient temperature and extracted with diethyl ether (3×250 ml). The aqueous phase was acidified with concentrated hydrochloric acid to about pH=1. The aqueous phase was extracted with dichloromethane (2×300 ml) and the combined organic phase was dried over Na2SO4. The solution was vacuum filtered and the filtrate was concentrated to an oil which solidified on standing. The solid was recrystallized from 300 ml of toluene to yield 72.16 g of crystals, m.p. 114°-116.5° C.

Workup

  1. temperaturethe mixture was heated for four hours (steam bath)
  2. extractionextracted with diethyl ether (3×250 ml)
  3. extractionThe aqueous phase was extracted with dichloromethane (2×300 ml)
  4. dry with materialthe combined organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated to an oil which
  7. customThe solid was recrystallized from 300 ml of toluene

Sources & evidence

ORD record
ord-099d796a7bd1492a9e4efd84c68331cc
Source dataset
uspto-grants-1988_05
Patent number
US04742171

Reaction notes

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