Hydrochloric Acid → HCID 15205888, compound

HRID 1377499Notes

Reaction equation

[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.[CH3:14][N:15]1[CH:20]2[CH2:21][CH2:22][CH:16]1[CH2:17][C:18](=[O:23])[CH2:19]2.Cl>CCCCCC.CCOCC>[F:13][C:10]1[CH:11]=[CH:12][C:7]([C:18]2([OH:23])[CH2:19][CH:20]3[N:15]([CH3:14])[CH:16]([CH2:22][CH2:21]3)[CH2:17]2)=[CH:8][CH:9]=1

Participants

Conditions

Temperature: -45 °C

Procedure

A mixture of dry ether (600 ml) and 15% BuLi in hexane (500 ml) was cooled to -45° C. A solution of 4-bromo-1-fluorobenzene (145 g) in dry ether (350 ml) was added dropwise at -45° C. followed by stirring for 1 h. A solution of 8-methyl-8-azabicyclo[3,2,1]octan-3-one (85 g) in dry ether (400 ml) was added dropwise at -50° C. followed by stirring for 30 min, the temperature raising to -20° C. The reaction mixture was poured into 2M hydrochloric acid and the phases separated. The ether phase was extracted with 2M hydrochloric acid and the combined aqueous phases made alkaline with aqueous NaOH. Extraction with ethyl acetate, drying of the organic phase over magnesium sulfate and removal of solvent in vacuo, gave 3-(4-fluorophenyl)-3-hydroxy-8-methyl-8-azabicyclo[3,2,1]octane (96 g) as a solid, mp: 169° C.

Workup

stirringby stirring for 30 min
temperaturethe temperature raising to -20° C
customthe phases separated
extractionThe ether phase was extracted with 2M hydrochloric acid
extractionExtraction with ethyl acetate
dry with materialdrying of the organic phase over magnesium sulfate and removal of solvent in vacuo

Sources & evidence

ORD record: ord-be4369a508df452299d8238780294275
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05665725

Reaction notes

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