HCID 86595841, compound → Ethyl (3R)-2-azabicyclo[2.2.2]octane-3-carboxylate

HRID 347815Notes

Reaction equation

C1([C@@H]([N:9]2[C@@H:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C@H:13]3[CH2:20][CH2:21][C@@H:10]2[CH:11]=[CH:12]3)C)C=CC=CC=1>C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[CH:10]12[CH2:11][CH2:12][CH:13]([CH2:20][CH2:21]1)[C@H:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[NH:9]2

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of ethyl (1R, 3R, 4S)-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.2]oct-5-ene-3-carboxylate (1.20 g, 4.17 mmol) in ethyl acetate (52 ml) was added 20 wt % Pd(OH)2 (0.878 g), and the mixture was stirred under a hydrogen atmosphere at 45° C. for 14 hours. After a filtration through Celite, the solvent was concentrated. The residue was purified by silica gel column chromatography (1%–5% methanol/chloroform), to give ethyl (3R)-2-azabicyclo [2.2.2]octane-3-carboxylate (0.362 g, 47%).

Workup

filtrationAfter a filtration through Celite
concentrationthe solvent was concentrated
customThe residue was purified by silica gel column chromatography (1%–5% methanol/chloroform)

Sources & evidence

ORD record: ord-2152fee1cf5b4f29bf64787d371f0142
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176217B2

Reaction notes

Loading…