HCID 86600512, compound → HCID 86600513, compound

HRID 1766395Notes

Reaction equation

HRID 1766395 reaction equation
C([N:8]1[CH2:17][CH2:16][CH:15]2[CH:10]([CH:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:12][CH:13]=[CH:14]2)[CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[CH2:9]1[CH:10]2[CH:15]([CH2:14][CH2:13][CH2:12][CH:11]2[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:16][CH2:17][NH:8]1

Participants

4

Reactant 1

HCID 86600512HCID 86600512, compound

Product 1

HCID 86600513HCID 86600513, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of ethyl (4aRS,8SR,8aSR)-2-benzyl-1,2,3,4,4a,7,8,8a-octahydroisoquinoline-8-carboxylate (440 mg, 1.47 mmol) in methanol (10 mL) was treated with 10% palladium on charcoal (20 mg) and stirred for 16 hours under an atmosphere of hydrogen. The mixture was filtered, and the filtrate was concentrated to provide a colorless oil (305 mg, 98%). 1H NMR (300 MHz, CDCl3) δ4.09 (q, J=7 Hz, 2H), 3.07 (m, 1H), 2.94 (dd, J=12, 4 Hz, 1H), 2.60 (m, 2H), 2.25 (J=12, 11 Hz, 1H), 2.0-1.7 (m, 3H), 1.6-1.2 (m, 6H), 1.91 (t, J=7 Hz, 3H), 1.10 (m, 2H). Mass spec (ES+) m/z 212.4 (M+H+, 100%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d25c29df04c24195b0666bd10cb9f308
Source dataset
uspto-grants-2007_06
Patent number
US07230022B2

Reaction notes

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