N-methyl-N-[((1S,2R)-1-phenyl-2-{[(phenylmethyl)oxy]methyl}cyclopropyl)methyl]benzenesulfonamide → N-{[(1S,2R)-2-(hydroxymethyl)-1-phenylcyclopropyl]methyl}-N-methylbenzenesulfonamide

HRID 2099273Notes

Reaction equation

HRID 2099273 reaction equation
[CH3:1][N:2]([CH2:12][C@@:13]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:15][C@H:14]1[CH2:16][O:17]CC1C=CC=CC=1)[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])=[O:4]>[Pd].CCOC(C)=O>[OH:17][CH2:16][C@@H:14]1[CH2:15][C@@:13]1([CH2:12][N:2]([CH3:1])[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])=[O:4])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 1

HCID 57794817N-methyl-N-[((1S,2R)-1-phenyl-2-{[(phenylmethyl)oxy]methyl}cyclopropyl)methyl]benzenesulfonamide

Product 1

HCID 57794737N-{[(1S,2R)-2-(hydroxymethyl)-1-phenylcyclopropyl]methyl}-N-methylbenzenesulfonamideYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

N-methyl-N-[((1S,2R)-1-phenyl-2-{[(phenylmethyl)oxy]methyl}cyclopropyl)methyl]benzenesulfonamide (1.57 g, 3.74 mmol), accessed via the method of preparation 6A, was combined with 10% palladium on activated carbon (0.35 g) in EtOAc and hydrogenated under 1 atm H2(g) for 4 h at ambient temperature. The catalyst was filtered off through celite and the filtrate concentrated to give the title product (1.17 g, 3.53 mmol, 95%) as a clear oil. 1H NMR (300 MHz, CDCl3) δ 7.68-7.18 (m, 10H), 4.07-4.03 (m, 1H), 3.72-3.66 (m, 1H), 3.55 (d, J=14.1 Hz, 1H), 3.25 (d, J=14.1 Hz, 1H), 2.36 (s, 3H), 1.59 (m, 1H), 1.18-1.15 (m, 1H), 0.79 (m, 1H). ES-LCMS m/z 354.3 (M+Na).

Workup

  1. filtrationThe catalyst was filtered off through celite
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-61e8da5e388049aa8509a8b236d0e9ea
Source dataset
uspto-grants-2009_08
Patent number
US07569579B2

Reaction notes

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