HCID 57504912, compound → HCID 57504913, compound

HRID 2060784Notes

Reaction equation

HRID 2060784 reaction equation
C([N:8]1[C:12]2([C:24]3[CH:25]=[C:26]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=4)[CH:27]=[CH:28][CH:29]=3)[CH2:13][CH:14]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:15][CH:11]2[CH2:10][O:9]1)C1C=CC=CC=1>[Pd].C(O)(=O)C>[NH2:8][C:12]1([C:24]2[CH:25]=[C:26]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=3)[CH:27]=[CH:28][CH:29]=2)[CH2:13][CH:14]([O:16][Si:17]([C:20]([CH3:21])([CH3:23])[CH3:22])([CH3:18])[CH3:19])[CH2:15][CH:11]1[CH2:10][OH:9]

Participants

4

Reactant 1

HCID 57504912HCID 57504912, compound

Product 1

HCID 57504913HCID 57504913, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 1-benzyl-5-(tert-butyldimethylsilyloxy)-6a-(3′-methoxybiphenyl-3-yl)hexahydro-1H-cyclopenta[c]isoxazole (2.04 g, 3.76 mmol) and palladium on carbon (0.400 g) in acetic acid (10 mL) is stirred at room temperature under hydrogen atmosphere (50 psi) for 19 hours. The reaction is filtered through a pad of diatomaceous earth and the filter cake is washed with methanol three times and the filtrate is concentrated under reduced pressure. The residue is dissolved in dichloromethane, the pH adjusted to pH 12 by addition of saturated aqueous sodium bicarbonate, and is extracted three times with dichloromethane. The combined organic layers are dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound. ES/MS m/e: 428 (M+1).

Workup

  1. filtrationThe reaction is filtered through a pad of diatomaceous earth
  2. washthe filter cake is washed with methanol three times
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. dissolutionThe residue is dissolved in dichloromethane
  5. additionthe pH adjusted to pH 12 by addition of saturated aqueous sodium bicarbonate
  6. extractionis extracted three times with dichloromethane
  7. dry with materialThe combined organic layers are dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a4e21c71e65e4845bad833665b6de944
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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