N-(benzenesulfonyl)-trans-4-azidoproline, methyl ester → N-(benzenesulfonyl)-trans-4-aminoproline, methyl ester

HRID 460276Notes

Reaction equation

HRID 460276 reaction equation
[C:1]1([S:7]([N:10]2[CH2:18][C@H:17]([N:19]=[N+]=[N-])[CH2:16][C@H:11]2[C:12]([O:14][CH3:15])=[O:13])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[Pd]>[C:1]1([S:7]([N:10]2[CH2:18][C@H:17]([NH2:19])[CH2:16][C@H:11]2[C:12]([O:14][CH3:15])=[O:13])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 58825074N-(benzenesulfonyl)-trans-4-azidoproline, methyl ester

Product 1

HCID 58825064N-(benzenesulfonyl)-trans-4-aminoproline, methyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.35 g (1.13 mmol) of 17 and 10% Pd/C (ca 50 mg) in 5 mL of methanol stirred under hydrogen (60 psi) overnight. The resulting mixture was filtered through a Celite plug and the filtrate concentrated to give 0.32 g (1.13 mmol, 100%) of 18 as a pale yellow syrup. Compound 18 was used without further purification. 1H-NMR (400 MHz, CDCl3, δ ppm) 7.86 (d, J=8 Hz, 2H), 7.57 (t, J=7 Hz, 1H), 7.51 (t, J=8 Hz, 2H), 4.40 (t, J=8 Hz, 1H), 3.68 (s, 3H), 3.63 (m, 1H), 3.69 (q, J=5 Hz, 1H), 3.05 (m, 1H), 2.13 (m, 1H), 1.91 (m, 1H), 1.59 (br s, 2H); 13C-NMR (400 MHz, CDCl3, 6 ppm) 172.79, 138.30, 133.35, 129.44, 127.94, 59.85, 56.26, 52.90, 51.01, 40.02; m/z: 285 (M+1)+.

Workup

  1. filtrationThe resulting mixture was filtered through a Celite plug
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-4e6b1ff9cff448188fad04f51ed2ab28
Source dataset
uspto-grants-2007_03
Patent number
US07196112B2

Reaction notes

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