649747-98-8 → Gabapentin Enacarbil

HRID 30514Notes

Reaction equation

HRID 30514 reaction equation
[C:1]([O:6][CH:7]([O:9][C:10]([NH:12][CH2:13][C:14]1([CH2:20][C:21]([O:23]CC2C=CC=CC=2)=[O:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:11])[CH3:8])(=[O:5])[CH:2]([CH3:4])[CH3:3].[H][H]>C(OCC)(=O)C.[Pd]>[C:1]([O:6][CH:7]([O:9][C:10]([NH:12][CH2:13][C:14]1([CH2:20][C:21]([OH:23])=[O:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:11])[CH3:8])(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 10025084649747-98-8HCID 178418361HCID 178418361, compound

Product 1

HCID 9883933Gabapentin Enacarbil

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Compound (10) (113 g) was dissolved in ethyl acetate (700 mL) and 10 g of 10% Pd—C was added. The reaction mixture was subjected to 50 psi of hydrogen gas in a Parr reactor for 40 min. Filtration through a sintered glass funnel and a hydrophobic membrane filtration cartridge (Millipore Opticap) removed the catalyst. The supernatant was concentrated to afford the product (11) as a white, crystalline solid (78 g, quantitative yield). Crystals formed in the freezer, then at room temperature over several days. 1H NMR (CDCl3, 400 MHz): 1.15 (d, 6H), 1.40-1.55 (m, 10H), 1.45 (d, 3H), 2.32 (s, 2H), 2.49-2.56 (m, 1H), 3.23 (d, 2H), 5.41 (t, 1H), 6.75 (q, 1H). MS(ESI) m/z 330.29 (M+H+).

Workup

  1. filtrationFiltration through a sintered glass funnel
  2. filtrationa hydrophobic membrane filtration cartridge (Millipore Opticap)
  3. customremoved the catalyst
  4. concentrationThe supernatant was concentrated

Sources & evidence

ORD record
ord-73d7796045b8420ea9181232f8fe6033
Source dataset
uspto-grants-2008_09
Patent number
US07423169B2

Reaction notes

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