Benzylamine → (2S,5R)-1-Benzyl-5-(ethoxycarbonyl)pyrrolidine-2-carboxylic acid

HRID 1527340Notes

Reaction equation

HRID 1527340 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][CH2:9][C@@H:8]([C:11]([O:13]CC)=[O:12])[N:7]1[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:5])[CH3:2].C(N)C1C=CC=CC=1>>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][CH2:9][C@@H:8]([C:11]([OH:13])=[O:12])[N:7]1[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 6932547(2S,5R)-Diethyl 1-benzylpyrrolidine-2,5-dicarboxylate

Product 1

HCID 68283039(2S,5R)-1-Benzyl-5-(ethoxycarbonyl)pyrrolidine-2-carboxylic acid

Procedure

The title compound was prepared according to the procedure described in Gazzetta Chimica Italiana, 1996, 126, 543-554 from (2R,5S)-1-benzyl-pyrrolidine-2,5-dicarboxylic acid diethyl ester prepared from benzylamine and diethyl meso-dibromoadipate according to the procedure described in J. Med. Chem. 2006, 49, 11, 3068-3076.

Sources & evidence

ORD record
ord-1b281f1bbcb348a2807231916d8a7038
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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