[1-(6'-Benzyloxy-[3,3']bipyridinyl-6-yl)-cyclopropyl]-carbamic acid tert-butyl ester → [1-(6'-Oxo-1',6'-dihydro-[3,3']bipyridinyl-6-yl)-cyclopropyl]-carbamic acid tert-butyl ester

HRID 2038795Notes

Reaction equation

HRID 2038795 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1([C:11]2[N:16]=[CH:15][C:14]([C:17]3[CH:18]=[N:19][C:20]([O:23]CC4C=CC=CC=4)=[CH:21][CH:22]=3)=[CH:13][CH:12]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1([C:11]2[N:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20](=[O:23])[NH:19][CH:18]=3)=[CH:13][CH:12]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67508567[1-(6'-Benzyloxy-[3,3']bipyridinyl-6-yl)-cyclopropyl]-carbamic acid tert-butyl ester

Product 1

HCID 68378938[1-(6'-Oxo-1',6'-dihydro-[3,3']bipyridinyl-6-yl)-cyclopropyl]-carbamic acid tert-butyl esterYield 104.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of [1-(6′-benzyloxy-[3,3′]bipyridinyl-6-yl)-cyclopropyl]-carbamic acid tert-butyl ester (0.20 g, 0.48 mmol) in MeOH (10 mL) was added Pd(OH)2 (0.2 g). The flask was purged with H2 gas and then H2 gas passed over the solution for 4 h. The mixture was filtered through diatomaceous earth and the filtrate was concentrated under reduced pressure to give [1-(6′-oxo-1′,6′-dihydro-[3,3′]bipyridinyl-6-yl)-cyclopropyl]-carbamic acid tert-butyl ester (0.16 g, 0.50 mmol), m/z 328.8 [M+H]+.

Workup

  1. customThe flask was purged with H2 gas
  2. filtrationThe mixture was filtered through diatomaceous earth
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d4de80745e5a47d99424276314628f8c
Source dataset
uspto-grants-2013_11
Patent number
US08575360B2

Reaction notes

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