(2S,4S)-4-azido-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid → (2S,4S)-4-Amino-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

HRID 893052Notes

Reaction equation

HRID 893052 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]>O.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 12094910(2S,4S)-4-azido-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

Product 1

HCID 14842624(2S,4S)-4-Amino-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl esterYield 91.1%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Azido acid 5b (1.10 g, 4.29 mmol) was dissolved in 100 ml 10% water/ethanol containing 150 mg Pd/C and hydrogenated at 100 psi for 16 h. The mixture was filtered through a pad of celite, washed with 50 mL of 1:1 water/ethanol and the filtrate concentrated to dryness. This material was recrystallized from water/ethanol to give 900 mg of 6 (84% yield), m.p.=225°-227° C. (decomp.) 1H NMR (D2O) δ 1.40/1.44 (m, 9H), 2.11 (m, 1H), 2.68 (m, 1H), 3.69 (m, 2H), 3.99 (m, 2H), 4.20 (dd, J=9.0/3.9 Hz, 1H). Anal. (C10H18N2O4.H2O) C, H, N.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. washwashed with 50 mL of 1:1 water/ethanol
  3. concentrationthe filtrate concentrated to dryness
  4. customThis material was recrystallized from water/ethanol

Sources & evidence

ORD record
ord-080f11ed812b410c8f905a51496e7454
Source dataset
uspto-grants-1992_06
Patent number
US05120859

Reaction notes

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