HCID 57794757, compound → HCID 57794775, compound

HRID 2099285Notes

Reaction equation

HRID 2099285 reaction equation
[C:1]1([C@@:7]2([CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[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][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 57794757HCID 57794757, compound

Product 1

HCID 57794775HCID 57794775, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1,1-dimethylethyl [((1R,2R)-1-phenyl-2-{[(phenylmethyl)oxy]methyl}cyclopropyl)methyl]carbamate (8.0 g, 21.7 mmol), accessed via the method of Preparation 11B, was combined with 10% palladium on activated carbon (0.8 g) in ethyl alcohol and hydrogenated under 1 atm H2(g) for 2.5 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 (5.8 g, 20.9 mmol, 96%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.35-7.25 (m, 5H), 3.52-3.48 (m, 1H), 3.35-3.30 (m, 1H), 3.23-3.19 (m, 1H), 3.10-3.07 (m, 1H), 1.45-1.37 (m, 11H), 1.04-1.04 (m, 1H), 0.87-0.84 (m, 1H). LCMS m/z 300.1 (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-b983f6b332184dd9ad5156105b203896
Source dataset
uspto-grants-2009_08
Patent number
US07569579B2

Reaction notes

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