Benzyl 10-cyano-2-cyclopentyldecanoate → 10-Cyano-2-cyclopentyldecanoic acid

HRID 977645Notes

Reaction equation

HRID 977645 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[C:12]([O:14]CC1C=CC=CC=1)=[O:13])#[N:2]>[Pd].CO>[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[C:12]([OH:14])=[O:13])#[N:2]

Participants

4

Reactant 1

HCID 10473415Benzyl 10-cyano-2-cyclopentyldecanoate

Product 1

HCID 1040065710-Cyano-2-cyclopentyldecanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of the cyanoester from step 3 (2.89 g, 8 mmol) and 10%, Pd-C (0.6 g, DeGussa, H2O content 50%) in anhyd MeOH (35 mL) was hydrogenated for 2 h (42-26 psi). The reaction mixture was filtered through a Celite® pad and concentrated to a colorless oil (2.02 g). 1H NMR (300 MHz, CDCl3) δ2.35(t, 8 Hz, 2H), 2.20 (m, 1H), 2.00(m, 1H), 1.3-1.9 (m, 22H).

Workup

  1. filtrationThe reaction mixture was filtered through a Celite® pad
  2. concentrationconcentrated to a colorless oil (2.02 g)

Sources & evidence

ORD record
ord-b27c3eb1d763404687ab654c33b26155
Source dataset
uspto-grants-1997_03
Patent number
US05614649

Reaction notes

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