Methanol → HCID 67740411, compound

HRID 580990Notes

Reaction equation

HRID 580990 reaction equation
[BH4-].[Na+].C([C:5]1[CH:6]=[C:7]([C:16]#[C:17][C:18]2([OH:26])[CH:23]3[CH2:24][CH2:25][N:20]([CH2:21][CH2:22]3)[CH2:19]2)[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH2:13][O:14][CH3:15])=O.[CH3:27][OH:28]>>[OH:28][CH2:27][C:8]1[CH:9]=[C:10]([O:11][CH2:12][CH2:13][O:14][CH3:15])[CH:5]=[CH:6][C:7]=1[C:16]#[C:17][C:18]1([OH:26])[CH:23]2[CH2:22][CH2:21][N:20]([CH2:25][CH2:24]2)[CH2:19]1

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86754165HCID 86754165, compound

Product 1

HCID 67740411HCID 67740411, compound

Procedure

Sodium borohydride (28.4 mg) was added to a solution of 3-[2-(3-formyl-4-(2-methoxyethoxy)phenyl)ethynyl]quinuclidin-3-ol in methanol at 0° C. The mixture was allowed to warm to ambient temperature and stirred for 1.5 hours. The reaction mixture was poured onto water (15 ml) and the mixture extracted with ethyl acetate (3×20 ml). The ethyl acetate extracts were combined, washed with brine solution (20 ml), dried (MgSO4) and evaporated. The residue was dissolved in acetonitrile (5 ml) and diethylether was added to give, on cooling, a solid (262 mg). This solid was further purified by crystallisation from acetonitrile to give 3-[2-(2-hydroxymethyl-4-(2-methoxyethoxy)phenyl)ethynyl]quinuclidin-3-ol (217 mg) as a solid, m.p. 98.5-100.0° C.; microanalysis, found C, 67.5%; H, 7.7%, N, 6.9%, C19H25NO4 0.8CH3CN requires: C, 67.9%; H, 7.6%; N, 6.9%; NMR(CDCl3): 1.40(1H,m), 1.65(1H,m), 2.0(3H,s), 2.05(3H,m), 2.8(4H,t), 3.03(1H,d), 3.28(1H,d), 3.45(3H,s), 3.75(2H,t), 4.13(2H,t), 4.72(2H,s), 6.78(1H,m), 7.05(1H,d) and 7.3(1H,t); m/z 332(M+H).

Workup

  1. additionThe reaction mixture was poured onto water (15 ml)
  2. extractionthe mixture extracted with ethyl acetate (3×20 ml)
  3. washwashed with brine solution (20 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. dissolutionThe residue was dissolved in acetonitrile (5 ml)
  7. additiondiethylether was added
  8. customto give
  9. temperatureon cooling
  10. customThis solid was further purified by crystallisation from acetonitrile

Sources & evidence

ORD record
ord-1dfbe11e2dc549c1bcafd7c155d3eb7c
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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