Hydrochloric Acid → HCID 15196231, compound

HRID 1449694Notes

Reaction equation

C([Li])CCC.CCCCCC.Br[C:13]1[CH:17]=[CH:16][O:15][CH:14]=1.[N:18]12[CH2:25][CH2:24][CH:21]([CH2:22][CH2:23]1)[C:20](=[O:26])[CH2:19]2.[Cl-].[NH4+].Cl>CCOCC>[O:15]1[CH:16]=[CH:17][C:13]([C:20]2([OH:26])[CH:21]3[CH2:24][CH2:25][N:18]([CH2:23][CH2:22]3)[CH2:19]2)=[CH:14]1

Participants

Conditions

Temperature: -75 °C

Procedure

A solution of n-butyllithium in hexane (14.2 mL, 1.5M, 21.3 mmol) was added dropwise to a solution of 3-bromofuran (2.2 mL, 23.9 mmol) in dry ether (40 mL) at -75° C. over 10 min. After 5 min., a solution of 3-quinuclidinone (2.66 g, 21.2 mmol) in dry ether (20 mL) was added, and the mixture was stirred at -75° C. for 4 hours. A solution of saturated aqueous ammonium chloride (1.5 mL) was added dropwise at -70° C., and the mixture was poured into 2.5M aqueous HCl and washed with ether. The aqueous layer was basified with 5M aqueous NaOH; the product was extracted with ether, dried (K2CO3), filtered, and concentrated in vacuo. Column chromatography on alumina, gradient eluted with CHCl3 →CHCl3 /MeOH (95:5), yielded 2.01 g (49%) of pure 3-(3-furyl)quinuclidin-3-ol, which was converted into the fumarate and recrystallized from acetone/MeOH; mp 207°-209° C.; Rf 0.21 in CHCl3 /MeOH on alumina. C11H15NO2.0.5C4H4O4 requires: C, 62.1; H, 6.8; N, 5.5. Found: C, 61.9; H, 6.9; N, 5.6.

Workup

washwashed with ether
extractionthe product was extracted with ether
dry with materialdried (K2CO3)
filtrationfiltered
concentrationconcentrated in vacuo
washColumn chromatography on alumina, gradient eluted with CHCl3 →CHCl3 /MeOH (95:5)

Sources & evidence

ORD record: ord-ef7951b563db4623ab151ac4d8b2b51e
Source dataset: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05599937

Reaction notes

Loading…