HCID 57794779, compound → HCID 57794787, compound

HRID 2099292Notes

Reaction equation

HRID 2099292 reaction equation
[C:1]1([C@@:7]2([CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:9][C@H:8]2[CH2:10][O:11]CC2C=CC=CC=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].C(O)C>[OH:11][CH2:10][C@@H:8]1[CH2:9][C@:7]1([CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 57794779HCID 57794779, compound

Product 1

HCID 57794787HCID 57794787, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1,1-dimethylethyl [2-((1R,2R)-1-phenyl-2-{[(phenylmethyl)oxy]methyl}cyclopropyl)ethyl]carbamate (5.9 g, 15.46 mmol), accessed via the method of Preparation 24B was combined with 10% palladium on activated carbon (600 mg) in 100 mL ethyl alcohol and hydrogenated under 1 atm H2(g) for 3 h at ambient temperature. The catalyst was filtered off through celite and the filtrate concentrated to give the title compound (4.1 g, 14.07 mmol, 91%) as a colorless oil. 1H NMR (400 MHz, DMSO-d6) δ 7.27-7.12 (m, 5H), 6.59-6.56 (m, 1H), 4.31-4.29 (m, 1H), 3.00-2.94 (m, 1H), 2.87-2.66 (m, 3H), 1.88-1.82 (m, 1H), 1.32-1.25 (m, 10H), 1.11-1.05 (m, 1H), 0.76-0.73 (m, 1H), 0.65-0.63 (m, 1H). ES-LCMS m/z 314.1 (M+Na).

Workup

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

Sources & evidence

ORD record
ord-32315436285846fca975c58efd674fc0
Source dataset
uspto-grants-2009_08
Patent number
US07569579B2

Reaction notes

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