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

HRID 1906446Notes

Reaction equation

HRID 1906446 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 13885244(+/-)-1-[(3-Fluorophenyl)methyl]-5-methoxycarbonyl-2-pyrrolidinone

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-435a2dd7863c4c1caa95573c4fc2057d
Source dataset
uspto-grants-1987_03
Patent number
US04652567

Reaction notes

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