HCID 86601547, compound → HCID 86601548, compound

HRID 853918Notes

Reaction equation

HRID 853918 reaction equation
[O:1]=[C:2]1[C:10]2([O:14][CH2:13][CH2:12][O:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:15]([N:18]3[CH2:22][CH2:21][CH2:20][C@H:19]3[CH2:23][O:24][O:25][CH3:26])(=[O:17])=[O:16])[CH:8]=2)[N:3]1[CH2:27][C:28]1([C:35]#[N:36])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.[H][H]>[Ni].N.CCO>[O:1]=[C:2]1[C:10]2([O:11][CH2:12][CH2:13][O:14]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:15]([N:18]3[CH2:22][CH2:21][CH2:20][C@H:19]3[CH2:23][O:24][O:25][CH3:26])(=[O:17])=[O:16])[CH:8]=2)[N:3]1[CH2:27][C:28]1([CH2:35][NH2:36])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

5

Reactant 2

HCID 86601547HCID 86601547, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86601548HCID 86601548, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 22020343Ethanol, reaction products with ammonia, distn. residuesSolvent

Procedure

A mixture of 1-{[2′-oxo-5′-{[(2S)-2-(methoxyoxymethyl)pyrrolidin-1-yl]sulfonyl}spiro[1,3-dioxolane-2,3′-indol]-1′(2′H)-yl]methyl}cycloheptanecarbonitrile (0.37 g, 0.74 mmol, 1 eq) and Raney Nickel (0.4 g) in 2N ammonia/EtOH (30 mL) was treated with hydrogen gas at 50 p.s.i. on a Parr Shaker Apparatus for 18 hours. The mixture was filtered to remove the catalyst. The catalyst was washed with 2N ammonia/EtOH and the combined filtrates were concentrated to yield the title compound as an oil (0.25 g, 68% yield). NMR (500 MHz, DMSO-d6): consistent. MS (API-ES+) m/z 508 [M+H].

Workup

  1. filtrationThe mixture was filtered
  2. customto remove the catalyst
  3. washThe catalyst was washed with 2N ammonia/EtOH
  4. concentrationthe combined filtrates were concentrated

Sources & evidence

ORD record
ord-57b166e833464b6a8a5b4ec881c9fb14
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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