9-((Z)-cyclooct-2-enyl)-3-oxa-9-azabicyclo[3.3.1]nonan-7-one → 3-Oxa-9-azabicyclo[3.3.1]nonan-7-one, 9-cyclooctyl-

HRID 84157Notes

Reaction equation

[CH:1]1([N:9]2[CH:14]3[CH2:15][C:16](=[O:18])[CH2:17][CH:10]2[CH2:11][O:12][CH2:13]3)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1>[Pd].CCO>[CH:1]1([N:9]2[CH:14]3[CH2:15][C:16](=[O:18])[CH2:17][CH:10]2[CH2:11][O:12][CH2:13]3)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 25 °C

Procedure

In a manner similar to Example 32, the compound of formula MG, 9-((Z)-cyclooct-2-enyl)-3-oxa-9-azabicyclo[3.3.1]nonan-7-one, was prepared from the compound of formula MF except that the compound of formula ME was used in place of the compound of formula JC (yield 90%). Under a hydrogen atmosphere, a mixture of the compound of formula MG, 5% palladium on carbon (1.0 g, Sigma-Aldrich), and EtOH (20 mL) was stirred at a temperature of about 25° C. for 4 h. After the Pd/C was filtered off, the filtrate was concentrated under reduced pressure to provide the compound of formula MH, 9-cyclooctyl-3-oxa-9-azabicyclo[3.3.1]nonan-7-one.

Workup

filtrationAfter the Pd/C was filtered off
concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-75a1a2b77b0046ca8480a7bc0a18d96a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846929B2

Reaction notes

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