Formaldehyde → HCID 67900871, compound

HRID 1681326Notes

Reaction equation

HRID 1681326 reaction equation
[H-].[Na+].[C:3]1([CH:9]([N:21]2[CH:25]=[N:24][N:23]=[N:22]2)[C:10]([O:12][C@@H:13]2[CH:18]3[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]3)[CH2:14]2)=[O:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:26]=[O:27].[Cl-].[NH4+]>O1CCCC1>[OH:27][CH2:26][C@:9]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)([N:21]1[CH:25]=[N:24][N:23]=[N:22]1)[C:10]([O:12][C@@H:13]1[CH:18]2[CH2:17][CH2:16][N:15]([CH2:20][CH2:19]2)[CH2:14]1)=[O:11]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 67901153HCID 67901153, compound

Product 1

HCID 67900871HCID 67900871, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (23 mg of an 80% dispersion in oil) was added to a mixture of (2RS,3R) 3-quinuclidinyl 2-phenyl-2-(1H-tetrazol-1-yl)acetate (see Preparation 5) (0.7 g) and paraformaldehyde (87 mg) in tetrahydrofuran (20 ml) at room temperature. After 1/2 hour saturated aqueous ammonium chloride was added, the tetrahydrofuran was evaporated under reduced pressure, and the aqueous residue extracted with ethyl acetate. The organic layer was dried over magnesium sulphate and evaporated under reduced pressure to leave a residue which was purified by chromatography on silica gel performing a gradient elution using dichloromethane pluse methanol 2→10% as eluant. Evaporation of appropriate fractions gave the two title compounds. Which isomer had 2R stereochemistry, and which 2S, was not assessed.

Workup

  1. customthe tetrahydrofuran was evaporated under reduced pressure
  2. extractionthe aqueous residue extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customto leave a residue which
  6. customwas purified by chromatography on silica gel performing
  7. washa gradient elution
  8. customEvaporation of appropriate fractions
  9. customgave the two title compounds

Sources & evidence

ORD record
ord-2576c8eeaabd498bada008f908c643f2
Source dataset
uspto-grants-1992_12
Patent number
US05171744

Reaction notes

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