4-(adamantan-2-yl(benzyloxy)methyl)-3-chloro-N-(methylsulfonyl)benzamide → 4-(adamantan-2-yl(hydroxy)methyl)-3-chloro-N-(methylsulfonyl)benzamide

HRID 1849753Notes

Reaction equation

HRID 1849753 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[CH:11]([O:26]CC1C=CC=CC=1)[C:12]1[CH:24]=[CH:23][C:15]([C:16]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[O:17])=[CH:14][C:13]=1[Cl:25])[CH2:8]2>CO.C(OCC)(=O)C.[Pd]>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[CH:11]([OH:26])[C:12]1[CH:24]=[CH:23][C:15]([C:16]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[O:17])=[CH:14][C:13]=1[Cl:25])[CH2:8]2

Participants

5

Reactant 1

HCID 867036344-(adamantan-2-yl(benzyloxy)methyl)-3-chloro-N-(methylsulfonyl)benzamide

Product 1

HCID 867036354-(adamantan-2-yl(hydroxy)methyl)-3-chloro-N-(methylsulfonyl)benzamideYield 28%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-(adamantan-2-yl(benzyloxy)methyl)-3-chloro-N-(methylsulfonyl)benzamide (0.290 g, 0.59 mmol) in methanol (10 mL) and ethyl acetate (10 mL) was added palladium on carbon (10%, 50 mg) and the reaction mixture was stirred for 2 hours under an atmosphere of hydrogen. The reaction mixture was filtered over diatomaceous earth, and the filtrate was concentrated in vacuo. The obtained residue was purified by reverse-phase preparative HPLC to afford the title compound as a colorless solid (0.065 g, 28%): 1H NMR (300 MHz, DMSO-d6) δ 12.20 (br s, 1H), 7.94 (s, 1H), 7.89 (d, J=7.2 Hz, 1H), 7.64 (d, J=7.1 Hz, 1H), 5.45 (br s, 1H), 5.23-5.14 (m, 1H), 3.31 (s, 3H), 2.37-2.27 (m, 1H), 2.11-1.35 (m, 13H), 1.11-1.01 (m, 1H); MS (ES−) m/z 396.2, 398.2 (M−1).

Workup

  1. filtrationThe reaction mixture was filtered over diatomaceous earth
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe obtained residue was purified by reverse-phase preparative HPLC

Sources & evidence

ORD record
ord-337cb476cd9342028ffb4328719e3bb1
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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