(S)-3-fluoropyrrolidine → (2R,5S)-4-Benzyl-5-((S)-3-fluoro-pyrrolidin-1-ylmethyl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 1475475Notes

Reaction equation

HRID 1475475 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH2:14]Cl)[N:11]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][C@H:9]1[CH3:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:24][C@H:25]1[CH2:29][CH2:28][NH:27][CH2:26]1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH2:14][N:27]2[CH2:28][CH2:29][C@H:25]([F:24])[CH2:26]2)[N:11]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][C@H:9]1[CH3:23])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 7016277(S)-3-fluoropyrrolidineHCID 86724019tert-butyl (2R,5R)-4-benzyl-5-(chloromethyl)-2-methylpiperazine-1-carboxylate

Product 1

HCID 70981376(2R,5S)-4-Benzyl-5-((S)-3-fluoro-pyrrolidin-1-ylmethyl)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

Procedure

The title compound was prepared following similar methods to those described in Preparation 352 starting from (2R,5R)-4-benzyl-5-chloromethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester (300 mg, 0.88 mmol) and (S)-3-fluoro-pyrrolidine (165 mg, 1.32 mmol). MS: [M+H]+=392.

Sources & evidence

ORD record
ord-4a7c7f52da60418b8ad35d8a55447eeb
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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