HCID 57794797, compound → HCID 57794763, compound

HRID 2099283Notes

Reaction equation

HRID 2099283 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 57794797HCID 57794797, compound

Product 1

HCID 57794763HCID 57794763, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1,1-dimethylethyl methyl[((1S,2R)-1-phenyl-2-{[(phenylmethyl)oxy]methyl}cyclopropyl)methyl]carbamate (20.65 g, 54 mmol), accessed via the method of Preparation 12A, was combined with 10% palladium on activated carbon (2.00 g) in 250 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 a yellow oil. The crude material was purified by flash chromatography on silica eluted with 5→25% EtOAc/DCM. Appropriate fractions were combined and concentrated to give the title compound (12.02 g, 41.2 mmol, 76%) as a colorless oil. 1H NMR (300 MHz, DMSO-d6, 90° C.) δ 7.30-7.22 (m, 9H), 7.15 (m, 1H), 4.41 (t, J=5.1 Hz, 1H), 3.87 (d, J=14.5 Hz, 1H), 3.74 (m, 1H), 3.52 (m, 1H), 3.31 (d, J=14.4 Hz, 1H), 2.63 (s, 3H), 1.21 (s, 9H), 1.20-1.07 (m, 2H), 0.77 (m, 1H). ES-LCMS m/z 314.21 (M+Na).

Workup

  1. filtrationThe catalyst was filtered off through celite
  2. concentrationthe filtrate concentrated to a yellow oil
  3. customThe crude material was purified by flash chromatography on silica
  4. washeluted with 5→25% EtOAc/DCM
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8b8fa16a78ef468da51a3aec5602c7f5
Source dataset
uspto-grants-2009_08
Patent number
US07569579B2

Reaction notes

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