(2S,4S)-4-azido-pyrrolidine-2-carboxylic acid ethyl ester trifluoroacetate salt → (2S,4S)-4-Amino-1-cyclopentylmethyl-pyrrolidine-2-carboxylic acid methyl ester

HRID 1477521Notes

Reaction equation

HRID 1477521 reaction equation
FC(F)(F)C(O)=O.C(OC([C@@H]1C[C@H](N=[N+]=[N-])CN1)=O)C.[CH3:21][O:22][C:23]([C@@H:25]1[CH2:29][C@H:28]([NH2:30])[CH2:27][N:26]1[CH2:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34]C1)=[O:24]>>[CH3:21][O:22][C:23]([C@@H:25]1[CH2:29][C@H:28]([NH2:30])[CH2:27][N:26]1[CH2:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34]1)=[O:24]

Participants

3

Reactant 2

HCID 89768579(2S,4S)-4-azido-pyrrolidine-2-carboxylic acid ethyl ester trifluoroacetate saltHCID 89776163(2S,4S)-4-amino-1-cyclohexylmethyl-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 117774563(2S,4S)-4-Amino-1-cyclopentylmethyl-pyrrolidine-2-carboxylic acid methyl ester

Procedure

(2S,4S)-4-Amino-1-cyclopentylmethyl-pyrrolidine-2-carboxylic acid methyl ester was prepared from (2S,4S)-4-azido-pyrrolidine-2-carboxylic acid ethyl ester trifluoroacetate salt in a similar reaction sequence used in the preparation of (2S,4S)-4-amino-1-cyclohexylmethyl-pyrrolidine-2-carboxylic acid methyl ester. MS calcd. for C13H25N2O2 [(M+H)+] 241, obsd. 241.

Sources & evidence

ORD record
ord-d373775753534f2199638dabc4633ac2
Source dataset
uspto-grants-2016_08
Patent number
US09403805B2

Reaction notes

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