HCID 14842622, compound → (2R,4S)-4-amino-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

HRID 893056Notes

Reaction equation

HRID 893056 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 14842622HCID 14842622, compound

Product 1

HCID 14842627(2R,4S)-4-amino-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidYield 116.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The trans azido acid 20b (2.0 g, 7.81 mmol) was hydrogenated as for the synthesis of 6, to give 2.1 g (97% yield) of 21 containing an equivalent of ethanol (by 1H NMR), after crystallization from ethanol, m.p.=225°-226° C. (decomp.) 1H NMR (CDCl3) δ 1.42/1.47 (2s, 9H), 2.28 (m, 1H), 2.45 (m, 1H), 3.58 (m, 1H), 3.80 (m, 1H), 3.99 (m, 1H), 4.24 (m, 1H). Anal. after high vacuum at 55° C. for 18 h; (C10H18N2O4.0.25 H2O) C, H, N.

Sources & evidence

ORD record
ord-fc1327c9b9144a2e8d69884adc2b1221
Source dataset
uspto-grants-1992_06
Patent number
US05120859

Reaction notes

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