Methanol → HCID 11955818, compound

HRID 334975Notes

Reaction equation

HRID 334975 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([O:15]CC2C=CC=CC=2)[C:12]([C:23]([CH3:25])=[CH2:24])=[CH:11][C:10]=1[C:26]([N:28]1[CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([O:37][CH2:38][CH2:39][N:40]([CH3:42])[CH3:41])[CH:34]=2)[CH2:29]1)=[O:27])C1C=CC=CC=1.[CH3:43]O>[Pd]>[OH:8][C:9]1[CH:14]=[C:13]([OH:15])[C:12]([CH:23]([CH3:24])[CH3:25])=[CH:11][C:10]=1[C:26]([N:28]1[CH2:36][C:35]2[C:30](=[C:31]([CH3:43])[CH:32]=[C:33]([O:37][CH2:38][CH2:39][N:40]([CH3:42])[CH3:41])[CH:34]=2)[CH2:29]1)=[O:27]

Participants

4

Reactant 2

HCID 887MethanolHCID 46916064(2,4-Bis-benzyloxy-5-isopropenyl-phenyl)-[5-(2-dimethylamino-ethoxy)-1,3-dihydro-isoindol-2-yl]-methanone

Product 1

HCID 11955818HCID 11955818, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(2,4-Bis-benzyloxy-5-isopropenyl-phenyl)-[5-(2-dimethylamino-ethoxy)-1,3-dihydro-isoindol-2-yl]-methanone (37 mg, 0.06 mmol) was hydrogenated in methanol at 50° C. over 10% palladium on charcoal using an H-cube hydrogenation apparatus, under free hydrogen conditions. The product was purified by preparative HPLC (basic method) to give the title compound as an off-white solid (9 mg, 35%). 1H NMR (MeOH-d4) 7.18 (1H, s), 6.77-6.65 (2H, br.m), 6.37 (1H, s), 4.85 (water obscuring CH2), 4.77 (2H, s), 4.08 (2H, t), 3.20 (1H, sept), 2.81 (2H, t), 2.39 (6H, s), 2.22 (3H, br.s), 1.21 (6H, d). MS: [M+H]+ 399.

Workup

  1. customThe product was purified by preparative HPLC (basic method)

Sources & evidence

ORD record
ord-e4de2f464bb940089728612001d4a063
Source dataset
uspto-grants-2014_11
Patent number
US08883790B2

Reaction notes

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