Sodium Hydroxide → HCID 57190678, compound

HRID 2294979Notes

Reaction equation

HRID 2294979 reaction equation
[OH-].[Al+3].[Li+].[OH-].[OH-].[OH-].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2([OH:24])[CH:21]3[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]3)[CH2:17]2)=[CH:10][CH:9]=1.[OH-].[Na+]>O1CCCC1>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]=[CH:15][C:16]2([OH:24])[CH:21]3[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]3)[CH2:17]2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 16206110Aluminate (Al(OH)41-), lithium, (T-4)-HCID 21472423HCID 21472423, compound

Product 1

HCID 57190678HCID 57190678, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1M solution of lithium aluminium hydroxide in tetrahydrofuran (3.0 ml) was added dropwise over 15 minutes to a stirred suspension of 3-[2-(4-bromophenyl)ethynyl]-3-hydroxyquinuclidine (918 mgs) in dry tetrahydrofuran (20 ml) at ambient temperature, under an atmosphere of argon. A complete solution formed as the addition progressed. The mixture was then stirred for 2 days at ambient temperature. A 2.0M solution of sodium hydroxide was then added dropwise to destroy the complex. The mixture was evaporated to dryness and the residue was purified by flash column chromatography on silica gel using 10% methanol in dichloromethane containing 1% ammonia (density, 0.88 g/cm3) to give [3-[2-(4-bromophenyl)-ethenyl]-3-hydroxyquinuclidine which was further purified by crystallisation from ethanol (210 mg) m.p. 218°-219° C.; NMR: 1.25(1H,m), 1.5(1H,m), 1.69(2H,m), 2.0(1H,m), 2.7(5H,m), 2.9(1H,d), 4.8(1H,s), 6.58(1H,d), 6.68(1H,d) and 7.42(4H,m).

Workup

  1. customA complete solution formed as the addition
  2. customto destroy the complex
  3. customThe mixture was evaporated to dryness
  4. customthe residue was purified by flash column chromatography on silica gel using 10% methanol in dichloromethane containing 1% ammonia (density, 0.88 g/cm3)

Sources & evidence

ORD record
ord-97366960b65d4c9b8ef3c73fb7297b08
Source dataset
uspto-grants-1997_11
Patent number
US05691349

Reaction notes

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