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

HRID 1477522Notes

Reaction equation

HRID 1477522 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:10][C:11]([C@@H:13]1[CH2:17][C@H:16]([N:18]=[N+]=[N-])[CH2:15][NH:14]1)=[O:12])[CH3:9].COC([C@@H]1C[C@H](N)CN1[CH2:31][CH:32]1[CH2:37]CCC[CH2:33]1)=O>>[CH2:8]([O:10][C:11]([C@@H:13]1[CH2:17][C@H:16]([NH2:18])[CH2:15][N:14]1[CH2:31][CH:32]([CH3:37])[CH3:33])=[O:12])[CH3:9]

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 89776131(2S,4S)-4-Amino-1-isobutyl-pyrrolidine-2-carboxylic acid ethyl ester

Procedure

(2S,4S)-4-Amino-1-isobutyl-pyrrolidine-2-carboxylic acid ethyl 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 C11H23N2O2 [(M+H)+] 215, obsd. 215.

Sources & evidence

ORD record
ord-862065a8a3ff484a8224d840ae22b758
Source dataset
uspto-grants-2016_08
Patent number
US09403805B2

Reaction notes

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