HCID 54353212, compound → HCID 53757529, compound

HRID 1682952Notes

Reaction equation

HRID 1682952 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]([C:26]#[N:27])([C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=1)[CH2:7][CH2:8][O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1)C>[Ni]>[CH:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:24]=[CH:25][C:16]=1[C:6]1([CH2:7][CH2:8][O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][O:11]2)[CH2:26][NH:27][C:4](=[O:3])[CH2:5]1

Participants

3

Reactant 1

HCID 54353212HCID 54353212, compound

Product 1

HCID 53757529HCID 53757529, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

3-Cyano-3-naphthalen-2-yl-5-(tetrahydro-pyran-2-yloxy)-pentanoic acid ethyl ester (003F143) (1.6154 g, 4.23 mmol) was hydrogenated at 40 psi over Raney nickel (10g) for 16 hours. The slurry was filtered and the filtrate was concentrated in vacuo. The residue was chromatographed on silica gel with a gradient from 50% ethyl acetate in hexane to 5% methanol in dichloromethane to give 0.8305 g (83%) of the title compound.

Workup

  1. filtrationThe slurry was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was chromatographed on silica gel with a gradient from 50% ethyl acetate in hexane to 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-b53f4ca02d694eca9909f553748d7e30
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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