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

HRID 1477519Notes

Reaction equation

HRID 1477519 reaction equation
FC(F)(F)C(O)=O.COC([C@@H]1C[C@H](N=[N+]=[N-])CN1)=O.[CH3:20][O:21][C:22]([C@@H:24]1[CH2:28][C@H:27]([NH2:29])[CH2:26][N:25]1[CH2:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)=[O:23]>>[CH3:20][O:21][C:22]([C@@H:24]1[CH2:28][C@H:27]([NH2:29])[CH2:26][N:25]1[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:23]

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 57674237(2S,4S)-4-Amino-1-benzyl-pyrrolidine-2-carboxylic acid methyl ester

Procedure

(2S,4S)-4-Amino-1-benzyl-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 C13H19N2O2 {(M+H)+} 235, obsd. 235.

Sources & evidence

ORD record
ord-e97c1f7a5c264397b781eeb6c2dace37
Source dataset
uspto-grants-2016_08
Patent number
US09403805B2

Reaction notes

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