HCID 57794808, compound → HCID 57794816, compound

HRID 2099284Notes

Reaction equation

HRID 2099284 reaction equation
[CH3:1][N:2]([CH2:10][C@:11]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:13][C@H:12]1[CH2:14][O:15]CC1C=CC=CC=1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6]>[Pd].C(O)C>[OH:15][CH2:14][C@@H:12]1[CH2:13][C@:11]1([CH2:10][N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:6])([CH3:7])[CH3:8])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 1

HCID 57794808HCID 57794808, compound

Product 1

HCID 57794816HCID 57794816, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1,1-dimethylethyl methyl[((1R,2R)-1-phenyl-2-{[(phenylmethyl)oxy]methyl}cyclopropyl)methyl]carbamate (3.1 g, 8.1 mmol), accessed via the method of Preparation 12B, was combined with 10% palladium on activated carbon (0.50 g) in ethyl alcohol and hydrogenated under 1 atm H2(g) for 0.5 h at ambient temperature. The catalyst was filtered off through celite and the filtrate concentrated to a colorless oil. The crude material was purified by flash chromatography (SiO2, eluted with EtOAc/hexanes (4:6)) to give the title compound (2.2 g, 7.5 mmol, 95%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.32-7.20 (m, 5H), 3.70-3.54 (m, 1H), 3.34-3.18 (m, 3H), 2.76-2.60 (m, 3H), 1.41-1.22 (m, 11H), 1.00 (m, 1H), 0.87-0.85 (m, 1H). ES-LCMS m/z 314.1 (M+Na).

Workup

  1. filtrationThe catalyst was filtered off through celite
  2. concentrationthe filtrate concentrated to a colorless oil
  3. customThe crude material was purified by flash chromatography (SiO2, eluted with EtOAc/hexanes (4:6))

Sources & evidence

ORD record
ord-e333d5cd9f074e79a17fd44d05e1f7f2
Source dataset
uspto-grants-2009_08
Patent number
US07569579B2

Reaction notes

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