HCID 117698840, compound → HCID 117697411, compound

HRID 1778476Notes

Reaction equation

HRID 1778476 reaction equation
C(OC([N:11]1[CH:16]2[CH2:17][CH:18]([CH:20]([OH:25])[C:21]([O:23][CH3:24])=[O:22])[CH2:19][CH:12]1[CH2:13][O:14][CH2:15]2)=O)C1C=CC=CC=1>CO.[Pd]>[CH3:24][O:23][C:21](=[O:22])[CH:20]([OH:25])[CH:18]1[CH2:19][CH:12]2[NH:11][CH:16]([CH2:15][O:14][CH2:13]2)[CH2:17]1

Participants

4

Reactant 1

HCID 117698840HCID 117698840, compound

Product 1

HCID 117697411HCID 117697411, compoundYield 57.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 7-(hydroxy-methoxycarbonyl-methyl)-3-oxa-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester (Compound AJ) (300 mg, 0.86 mmol) and 10% palladium on active carbon (100 mg) in methanol (10 mL) was stirred at room temperature under hydrogen (30 psi) for 16 hours. The catalyst was filtered off. The filtrate was concentrate in vacuo to afford hydroxy-(3-oxa-9-aza-bicyclo[3.3.1]non-7-yl)-acetic acid methyl ester (Compound AH) (107 mg, 57%) which was used for the next step without further purification. MS: calc'd (MH+) 216, measured (MH+) 216.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationThe filtrate was concentrate in vacuo

Sources & evidence

ORD record
ord-cb0f9cc07a634c5a8e551459bc8ce843
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

Loading…