HCID 68682712, compound → HCID 68682186, compound

HRID 2263630Notes

Reaction equation

HRID 2263630 reaction equation
[CH:1]1([CH2:4][S:5]([CH:8]2[CH2:13][CH2:12][C:11]([C:16]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:17])([C:14]#[N:15])[CH2:10][CH2:9]2)(=[O:7])=[O:6])[CH2:3][CH2:2]1>N.CO.[Ni]>[NH2:15][CH2:14][C:11]1([C:16]([N:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)=[O:17])[CH2:12][CH2:13][CH:8]([S:5]([CH2:4][CH:1]2[CH2:3][CH2:2]2)(=[O:6])=[O:7])[CH2:9][CH2:10]1

Participants

5

Reactant 1

HCID 68682712HCID 68682712, compound

Product 1

HCID 68682186HCID 68682186, compoundYield 103%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

To 4-cyclopropylmethanesulfonyl-1-(pyrrolidine-1-carbonyl)-cyclohexanecarbonitrile (231 mg; 0.712 mmol) in 2 M ammonia in methanol solution (15 ml) under a nitrogen atmosphere was added Raney Nickel (approx. 1 ml of 50% aqueous slurry). The resulting mixture was agitated under an atmosphere of hydrogen (50 psi) on a Parr apparatus for 18 hours. The mixture was filtered through a catalyst filter and the catalyst washed extensively with MeOH (200 ml, added in portions). The filtrate was evaporated in vacuo to give the product as a pale green oil (241 mg). m/z=329 (M+H+).

Workup

  1. filtrationThe mixture was filtered through a catalyst
  2. filtrationfilter
  3. washthe catalyst washed extensively with MeOH (200 ml, added in portions)
  4. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-489c215786794042a0743ad94a526afb
Source dataset
uspto-grants-2010_12
Patent number
US07851638B2

Reaction notes

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