HCID 54192391, compound → HCID 22873790, compound

HRID 1683876Notes

Reaction equation

HRID 1683876 reaction equation
C(OC([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([CH:26]=[CH:27][S:28]([CH2:31][CH3:32])(=[O:30])=[O:29])[CH:24]=2)[NH:19][CH:18]=1)=O)C1C=CC=CC=1>C(O)C.[Pd]>[CH2:31]([S:28]([CH2:27][CH2:26][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[C:17]2[CH2:16][C@H:12]1[CH2:13][CH2:14][CH2:15][NH:11]1)(=[O:30])=[O:29])[CH3:32]

Participants

4

Reactant 1

HCID 54192391HCID 54192391, compound

Product 1

HCID 22873790HCID 22873790, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-(N-benzyloxycarbonyl-2(R)-pyrrolidinylmethyl)-5-(2-ethylsulphonylethenyl)-1H-indole (Preparation 3; 160 mg, 0.35 mmol) in ethanol (5 ml) was hydrogenated over 10% palladium on charcoal (150 mg) at 15 p.s.i. (1.04 bar) and room temperature for 18 hours, and then filtered. Evaporation of the filtrate under reduced pressure yielded a foam which was purified by column chromatography on silica gel, eluting with a gradient of 0.880 aqueous ammonia: methanol:dichloromethane (0:10:90 to 1:10:90), to provide the title compound as a foam (70 mg). Rf 0.30 (SS 4). [α]D25 -11° (c=0.1, CH3OH). Found: C,63.13; H,7.37; N,8.55. C17H24N2O2S; 0.05 CH2Cl2 requires C,63.07; H,7.48; N,8.63%. δ(CDCl3): 1.35(3H,t), 1.65-1.90(5H,m), 2.70-3.10(6H,m), 3.25(4H,m), 3.35(1H,m), 5.25(0.10H,s, CH2Cl2), 6.98-7.04(2H,m), 7.22(1H,d), 7.45(1H,s), 8.12(1H,br s).

Workup

  1. filtrationfiltered
  2. customEvaporation of the filtrate under reduced pressure
  3. customyielded a foam which
  4. customwas purified by column chromatography on silica gel
  5. washeluting with a gradient of 0.880 aqueous ammonia: methanol:dichloromethane (0:10:90 to 1:10:90)

Sources & evidence

ORD record
ord-8e37f6aa0dee42f1b2e14aeef1f1dbbf
Source dataset
uspto-grants-1997_06
Patent number
US05639779

Reaction notes

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