Methanol → HCID 67740237, compound

HRID 580989Notes

Reaction equation

HRID 580989 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:5][C:4]=1[C:15]#[C:16][C:17]1([OH:25])[CH:22]2[CH2:23][CH2:24][N:19]([CH2:20][CH2:21]2)[CH2:18]1)=[O:2].CO.[BH4-].[Na+]>O>[OH:2][CH2:1][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:5][C:4]=1[C:15]#[C:16][C:17]1([OH:25])[CH:22]2[CH2:21][CH2:20][N:19]([CH2:24][CH2:23]2)[CH2:18]1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86754164HCID 86754164, compound

Product 1

HCID 67740237HCID 67740237, compoundYield 27.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-[2-(2-formyl-4-(2-methoxycarbonylethyl)phenyl]ethynyl]quinuclidin-3-ol (575 mg) was stirred with methanol (25 ml) at ambient temperature under an atmosphere of argon. Sodium borohydride (329 mg) was added portionwise over 5 minutes to the reaction mixture and stirring continued at ambient temperature overnight. Water (25 ml) was added and the mixture was extracted with ethyl acetate (25 ml). The organic phase was separated, washed with saturated aqueous sodium carbonate (3×25 ml), water (3×25 ml), dried (MgSO4) and evaporated. The residue was purified by elution through silica gel (10 g Bond elut column) with a gradient of 0-30% methanol in dichloromethane to give 3-[2-(2-hydroxymethyl-4-(2-methoxycarbonylethyl)phenyl)ethynyl]quinuclidin-3-ol (160 mg) as a solid, m.p. 35.8° C.; microanalysis, found: C, 69.2; H, 7.5; N, 3.9% C20H25NO4 0.2 H2O requires: C, 69.2; H, 7.38; N, 4.04%; NMR(CDCl3): 1.4(1H,m), 1.66(1H,m), 2.02(3H,m), 2.62(2H,t), 2.8(3H,m), 2.95(2H,t), 3.03(1H,d), 3.27(1H,d), 3.66(3H,s), 4.75(2H,s), 7.07(1H,m) and 7.3(2H,m); m/z 344 (M+H).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (25 ml)
  2. customThe organic phase was separated
  3. washwashed with saturated aqueous sodium carbonate (3×25 ml), water (3×25 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by elution through silica gel (10 g Bond elut column) with a gradient of 0-30% methanol in dichloromethane

Sources & evidence

ORD record
ord-b06abaadc0504c88a086a9cfda92585b
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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