Methanol → HCID 11184346, compound

HRID 130396Notes

Reaction equation

HRID 130396 reaction equation
C([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11]([C:17]1[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=1)([OH:16])[CH2:12]2)C1C=CC=CC=1.C([O-])=O.[NH4+].CO>[Pd].C(Cl)(Cl)Cl.CO>[CH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:25]=[CH:26][C:17]=1[C:11]1([OH:16])[CH2:12][CH:13]2[NH:8][CH:9]([CH2:15][CH2:14]2)[CH2:10]1

Participants

6

Reactant 3

HCID 887MethanolHCID 2723923Ammonium formateHCID 22562217HCID 22562217, compound

Product 1

HCID 11184346HCID 11184346, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584188Chloroform methanolSolvent

Conditions

Temperature
50 °C

Procedure

To 3.80 g (11.1 mmol) 8-benzyl-3-naphthalen-2-yl-8-aza-bicyclo[3.2.1]octan-3-ol was added 1.20 g (19.0 mmol) of ammonium formate, 100 mL MeOH, and 2.46 g Pd/C (10 wt. %). The reaction mixture was heated to 50° C., and was monitored by TLC on a SiO2 plate with CHCl3:MeOH (10:1). After 21 h, the mixture was cooled to room temperature, filtered through a pad of celite and evaporated to afford 2.0 g (7.9 mmol, a 72% yield) of the title compound as an off-white solid. MS (ES) m/z: 344 (MH)+.

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. filtrationfiltered through a pad of celite
  3. customevaporated
  4. customto afford 2.0 g (7.9 mmol

Sources & evidence

ORD record
ord-d45862d990ed48b8a3c6f130428dab5b
Source dataset
uspto-grants-2008_06
Patent number
US07381723B2

Reaction notes

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