(2S,4R)-4-tert-butoxy-2-oxazol-2-yl-pyrrolidine-1-carboxylic acid benzyl ester → (2S,4S)-4-Amino-2-oxazol-2-yl-pyrrolidine-1-carboxylic acid benzyl ester

HRID 1477529Notes

Reaction equation

HRID 1477529 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14](OC(C)(C)C)[CH2:13][C@H:12]1[C:21]1[O:22][CH:23]=[CH:24][N:25]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC([C@@H]1C[C@H](N)C[N:31]1CC1CCCCC1)=O>>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@@H:14]([NH2:31])[CH2:13][C@H:12]1[C:21]1[O:22][CH:23]=[CH:24][N:25]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 59548492(2S,4R)-4-tert-butoxy-2-oxazol-2-yl-pyrrolidine-1-carboxylic acid benzyl esterHCID 89776163(2S,4S)-4-amino-1-cyclohexylmethyl-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 89768242(2S,4S)-4-Amino-2-oxazol-2-yl-pyrrolidine-1-carboxylic acid benzyl ester

Procedure

(2S,4S)-4-Amino-2-oxazol-2-yl-pyrrolidine-1-carboxylic acid benzyl ester was prepared from (2S,4R)-4-tert-butoxy-2-oxazol-2-yl-pyrrolidine-1-carboxylic acid benzyl 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 C15H18N3O3 [(M+H)+] 288, obsd. 288.

Sources & evidence

ORD record
ord-e33618dad65e45ef8ccabb205fc8807e
Source dataset
uspto-grants-2016_08
Patent number
US09403805B2

Reaction notes

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