7-Methanesulfonyl-3-oxa-7,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester → 7-Methanesulfonyl-3-oxa-7,9-diaza-bicyclo[3.3.1]nonane

HRID 1778466Notes

Reaction equation

HRID 1778466 reaction equation
C(OC([N:11]1[CH:16]2[CH2:17][N:18]([S:20]([CH3:23])(=[O:22])=[O:21])[CH2:19][CH:12]1[CH2:13][O:14][CH2:15]2)=O)C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH3:23][S:20]([N:18]1[CH2:17][CH:16]2[NH:11][CH:12]([CH2:13][O:14][CH2:15]2)[CH2:19]1)(=[O:22])=[O:21]

Participants

5

Reactant 2

HCID 1176975127-Methanesulfonyl-3-oxa-7,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 1176978897-Methanesulfonyl-3-oxa-7,9-diaza-bicyclo[3.3.1]nonaneYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the crude Compound Y in MeOH (20 mL) was added 10% Pd on carbon (20 mg). The mixture was stirred under one atmosphere pressure of hydrogen at room temperature. After the reaction was completed, the mixture was filtered and concentrated to give 7-methanesulfonyl-3-oxa-7,9-diaza-bicyclo[3.3.1]nonane (Compound W) (50 mg, 78%) which was directly used for next step. MS: calc'd (MH+) 207, measured (MH+) 207.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-e82419ec77e2469db9513c47986dfb8f
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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