Benzyltrimethylammonium hydroxide → (R)-4-Acetyl-1-((S)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one

HRID 1496846Notes

Reaction equation

[C:1]([CH:4]1[CH2:8][N:7]([C@H:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH3:10])[C:6](=[O:19])[CH2:5]1)(=[O:3])[CH3:2].[OH-].C([N+](C)(C)C)C1C=CC=CC=1>C(O)CCC>[C:1]([C@H:4]1[CH2:8][N:7]([C@H:9]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)[CH3:10])[C:6](=[O:19])[CH2:5]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

103 g of a mixture of diastereoisomers (R/S)-4-acetyl-1-[(S)-1-(4-methoxyphenyl)-ethyl]-pyrrolidine-2-one is dissolved in 155 mL 1-butanol at 25° C. 18 mL benzyltrimethylammonium hydroxide (40% solution in methanol) is added. The solution is stirred for 30 minutes at 25° C. The solution is cooled to 0° C. Precipitation starts. The suspension is stirred for 15 minutes at 0° C. 100 mL n-heptane is added slowly and the suspension is stirred for 30 minutes at 0° C. The addition of 100 mL portions of n-heptane is repeated 4 times with subsequent stirring of the suspension at 0° C. for 30 minutes. The precipitate is isolated, washed with n-heptane and dried at 50° C.

Workup

temperatureThe solution is cooled to 0° C
customPrecipitation
stirringThe suspension is stirred for 15 minutes at 0° C
addition100 mL n-heptane is added slowly
stirringthe suspension is stirred for 30 minutes at 0° C
additionThe addition of 100 mL portions of n-heptane
stirringwith subsequent stirring of the suspension at 0° C. for 30 minutes
customThe precipitate is isolated
washwashed with n-heptane
customdried at 50° C.

Sources & evidence

ORD record: ord-49adb01a055842c6a4d0b067a176f558
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199937B2

Reaction notes

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