N-Boc-cis-4-hydroxy-L-proline methyl ester → (2S,4R)-4-Amino-1-cyclohexylmethyl-pyrrolidine-2-carboxylic acid methyl ester

HRID 1477523Notes

Reaction equation

HRID 1477523 reaction equation
COC([C@@H]1C[C@H](O)CN1C(OC(C)(C)C)=O)=O.[CH3:18][O:19][C:20]([C@@H:22]1[CH2:26][C@H:25]([NH2:27])[CH2:24][N:23]1[CH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)=[O:21]>>[CH3:18][O:19][C:20]([C@@H:22]1[CH2:26][C@@H:25]([NH2:27])[CH2:24][N:23]1[CH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)=[O:21]

Participants

3

Reactant 2

HCID 10752873N-Boc-cis-4-hydroxy-L-proline methyl esterHCID 89776163(2S,4S)-4-amino-1-cyclohexylmethyl-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 89776174(2S,4R)-4-Amino-1-cyclohexylmethyl-pyrrolidine-2-carboxylic acid methyl ester

Procedure

(2S,4R)-4-Amino-1-cyclohexylmethyl-pyrrolidine-2-carboxylic acid methyl ester was prepared from (2S,4S)-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 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-9d66e5dafbf543248a667fa54fda2af5
Source dataset
uspto-grants-2016_08
Patent number
US09403805B2

Reaction notes

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