HCID 54116374, compound → HCID 18373597, compound

HRID 2301485Notes

Reaction equation

HRID 2301485 reaction equation
[C:1]12([CH:11]=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:13]#[N:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2>CCOC(C)=O.[Pd]>[C:1]12([CH2:11][CH:12]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:13]#[N:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

4

Reactant 1

HCID 54116374HCID 54116374, compound

Product 1

HCID 18373597HCID 18373597, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(1-adamantyl)-2-phenylpropenenitrile (600 mg, 2.28 mmol) in EtOAc (30 mL) was treated with 10% Pd/C (70 mg), hydrogenated at 50 psi for 16 h, filtered through SiO2 and concentrated in vacuo. The residue was purified by chromatography [SiO2, EtOAc-heptane (1:1)] and the resulting solid recrystallised (heptane) to give the product (552 mg, 91%) as a white crystalline solid: mp 83-84° C; IR νmax (Nujol)/cm−1 2912, 2852, 2239, 1497, 1453, 1377, 1355, 1346, 1105, 749, 713 and 696; NMR δH (400 MHz, CDCl3) 1.50 (1H, dd, J 14.3, 3.2 Hz), 1.63 (9H, m), 1.72 (3H, m), 1.94 (1H, dd, J 14.3,10.4 Hz), 2.01 (3H, m), 3.79 (1H, dd, J 10.4, 3.2 Hz) and 7.35 (5H, m); Anal. Calcd for C19H23N: C, 85.99; H, 8.73; N, 5.28. Found: C, 85.96; H, 8.90; N, 5.27.

Workup

  1. filtrationfiltered through SiO2
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by chromatography [SiO2, EtOAc-heptane (1:1)]
  4. customthe resulting solid recrystallised (heptane)

Sources & evidence

ORD record
ord-5e1afc9cf5214dd6b713040b61f08d57
Source dataset
uspto-grants-2002_12
Patent number
US06500866B1

Reaction notes

Loading…