HCID 86594365, compound → HCID 69035635, compound

HRID 351381Notes

Reaction equation

HRID 351381 reaction equation
[N:1]([C@@H:4]1[CH2:9][CH2:8][C@H:7]([N:10]2[CH2:14][CH2:13][C@H:12]([CH2:15][C:16]3([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=4)[O:20][CH2:19][CH2:18][O:17]3)[C:11]2=[O:31])[C@H:6]([CH2:32][S:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)(=[O:35])=[O:34])[CH2:5]1)=[N+]=[N-]>CO.[Pd]>[NH2:1][C@@H:4]1[CH2:9][CH2:8][C@H:7]([N:10]2[CH2:14][CH2:13][C@H:12]([CH2:15][C:16]3([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[CH:22]=4)[O:17][CH2:18][CH2:19][O:20]3)[C:11]2=[O:31])[C@H:6]([CH2:32][S:33]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)(=[O:34])=[O:35])[CH2:5]1

Participants

4

Reactant 1

HCID 86594365HCID 86594365, compound

Product 1

HCID 69035635HCID 69035635, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 39g-b (222 mg, 375 μmol) and 10% Pd/C (239 mg, 112 μmol) in MeOH (150 mL) was hydrogenated (50 psi) for 2 h. The mixture was filtered through diatomaceous earth (infusorial earth) and the filtrate was evaporated under vacuum to give (R*)-1-((1S*,2R*,4R*)-4-amino-2-(phenylsulfonylmethyl)cyclohexyl)-3-((2-(3-(trifluoromethyl)phenyl)-1,3-dioxolan-2-yl)methyl)pyrrolidin-2-one (39h-b, 169 mg, 80%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.87 (d, J=7.3 Hz, 2H), 7.68–7.35 (m, 7H), 4.22 (s, 1H), 4.02–3.60 (m, 5H), 3.50–3.14 (m, 4H), 2.80–2.63 (m, 1H), 2.60–1.60 (m, 12H); 19F NMR (282 MHz, CDCl3) δ −62.8; ESI MS m/z 567 [C28H33F3N2O5S+H]+.

Workup

  1. customfor 2 h
  2. filtrationThe mixture was filtered through diatomaceous earth (infusorial earth)
  3. customthe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-8cd2569bccbb44988e08becfd05c296d
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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