1-(1,1-Dimethylethyl) (2S,4R)-4-azido-1,2-pyrrolidinedicarboxylate → (2S,4R)-4-amino-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

HRID 893054Notes

Reaction equation

HRID 893054 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][C@H:14]([N:16]=[N+]=[N-])[CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:15][C@H:14]([NH2:16])[CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 148426211-(1,1-Dimethylethyl) (2S,4R)-4-azido-1,2-pyrrolidinedicarboxylate

Product 1

HCID 14842625(2S,4R)-4-amino-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The trans azido acid 8b (3.0 g., 11.7 mmol) was hydrogenated as for the synthesis of 6, to give 1.8 g (67% yield) after crystlalization from ethanol, m.p.=228°-229° C. (decomp.). 1H NMR (CDCl3) δ1.42/1.47 (2s, 9H), 2.29 (m, 1H), 2.45 (m, 1H), 3.58 (m, 1H), 3.80 (m, 1H), 3.99 (m, 1H), 4.24 (m, 1H). Anal. (C10H18N2O4.0.5H2O) C, H, N.

Sources & evidence

ORD record
ord-ab4b858d18054a4e882577fdf6d6a567
Source dataset
uspto-grants-1992_06
Patent number
US05120859

Reaction notes

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