Sodium Hydroxide → (+/-)-3-(6-Methoxy-naphthalen-2-yl)-1-aza-bicyclo[2.2.2]octan-3-ol

HRID 910206Notes

Reaction equation

C([Li])CCC.Br[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=2)[CH:8]=1.[N:19]12[CH2:26][CH2:25][CH:22]([CH2:23][CH2:24]1)[C:21](=[O:27])[CH2:20]2.[OH-].[Na+]>O.C(OCC)C>[CH3:18][O:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:21]1([OH:27])[CH:22]3[CH2:25][CH2:26][N:19]([CH2:24][CH2:23]3)[CH2:20]1)[CH:16]=[CH:15]2

Participants

Conditions

Temperature: -70 °C

Procedure

Butyllithium (2.5 M, 1.86 ml, 4.64 mmol) was added to a mixture of 2-bromo-6-methoxynaphthalene (1.0 g, 4.22 mmol) and diethyl ether (10 ml) at 20° C. The temperature was kept below 35° C. for 30 min. The mixture was cooled to −70° C. and 3-quinuclidinone (0.53 g, 4.22 mmol) was added at −70° C. The mixture was stirred at −70° C. for 1 h. The mixture was allowed to reach room temperature. Water (1 ml) was added followed by aqueous sodium hydroxide (1 M, 10 ml). The crystalline product was filtered and was washed with cold diethyl ether (2 ml). Yield 0.49 g (41%). Mp >330° C.

Workup

customto reach room temperature
filtrationThe crystalline product was filtered
washwas washed with cold diethyl ether (2 ml)

Sources & evidence

ORD record: ord-04c094d2c82b424d985c0fc44bdfc7b0
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022081B2

Reaction notes

Loading…