Water → HCID 67851393, compound

HRID 580957Notes

Reaction equation

HRID 580957 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:20]2([OH:28])[CH:25]3[CH2:26][CH2:27][N:22]([CH2:23][CH2:24]3)[CH2:21]2)=[CH:14][CH:13]=1.O.[OH-].[Na+]>O1CCCC1>[CH3:7][O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15](/[CH:18]=[CH:19]/[C:20]2([OH:28])[CH:25]3[CH2:26][CH2:27][N:22]([CH2:23][CH2:24]3)[CH2:21]2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67740377HCID 67740377, compound

Product 1

HCID 67851393HCID 67851393, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1M solution of lithium aluminium hydride in tetrahydrofuran (10 ml) was added over a period of 20 minutes to a stirred solution of 3-[2-{4-(2-methoxyethoxy)phenyl}ethynyl]quinuclidin-3-ol (3.01 g) in dry tetrahydrofuran (100 ml) under an atmosphere of argon at 40° C. The reaction mixture was then stirred at ambient temperature for 16 hours. Water (0.4 ml) and 2M aqueous sodium hydroxide solution (0.8 ml) was then added to the reaction mixture dropwise followed by a further quantity of water (1.2 ml). The resulting precipitate was collected by filtration and the filtrate was evaporated. The residue from the filtrate was crystallised from acetonitrile to give 3-[(E)-2-{4-(2-methoxyethoxy)phenyl}vinyl]quinuclidin-3-ol (2.54 g) as a solid, mp 164-166° C., microanalysis, found C,71.4; H,8.6; N,4.5%; C18H25NO3 requires: C,71.3; H,8.31; N,4.62%; NMR ([CD3 ]2SO): 1.15-1.32 (1H, m), 1.38-1.52 (1H, m), 1.62-1.74 (2H, m), 1.95-2.1 (1H, m), 2.58-2.6 (5H, m), 2.82-2.92 (1H, d), 3.3 (3H, s), 3.6-3.67 (2H, m), 4.03-4.1 (2H, m), 4.66 (1H, s), 6.38-6.45 (1H, d, J=16.67), 6.51-6.58 (1H, d, J=16.67), 6.86-7.12 (2H, d) and 7.32-7.38 (2H, d); m/z 304 (M+H).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customthe filtrate was evaporated
  3. customThe residue from the filtrate was crystallised from acetonitrile

Sources & evidence

ORD record
ord-53f403f819df4ad1a99af7fbcc42262a
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

Loading…