(2S,4S)-4-azido-pyrrolidine-2-carboxylic acid methyl ester trifluoro-acetate salt → (2S,4S)-4-Amino-1-(3,3-dimethyl-butyl)-pyrrolidine-2-carboxylic acid methyl ester

HRID 1477520Notes

Reaction equation

HRID 1477520 reaction equation
F[C:2](F)(F)C(O)=O.[CH3:8][O:9][C:10]([C@@H:12]1[CH2:16][C@H:15]([N:17]=[N+]=[N-])[CH2:14][NH:13]1)=[O:11].COC([C@@H]1C[C@H](N)CN1[CH2:30][CH:31]1[CH2:36][CH2:35]CC[CH2:32]1)=O>>[CH3:8][O:9][C:10]([C@@H:12]1[CH2:16][C@H:15]([NH2:17])[CH2:14][N:13]1[CH2:35][CH2:36][C:31]([CH3:2])([CH3:32])[CH3:30])=[O:11]

Participants

3

Reactant 2

HCID 89768308(2S,4S)-4-azido-pyrrolidine-2-carboxylic acid methyl ester trifluoro-acetate saltHCID 89776163(2S,4S)-4-amino-1-cyclohexylmethyl-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 89776135(2S,4S)-4-Amino-1-(3,3-dimethyl-butyl)-pyrrolidine-2-carboxylic acid methyl ester

Procedure

(2S,4S)-4-Amino-1-(3,3-dimethyl-butyl)-pyrrolidine-2-carboxylic acid methyl ester was prepared from (2S,4S)-4-azido-pyrrolidine-2-carboxylic acid methyl 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 C12H25N2O2 [(M+H)+] 229, obsd. 229.

Sources & evidence

ORD record
ord-805e4ebec1b54b29b9c77906b5cbb46a
Source dataset
uspto-grants-2016_08
Patent number
US09403805B2

Reaction notes

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