Water → (1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)methanol

HRID 1879832Notes

Reaction equation

HRID 1879832 reaction equation
[C:1]1([CH2:7][N:8]2[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]2Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].O>CO>[C:1]1([CH2:7][N:8]2[CH2:9][CH:10]=[C:11]([CH2:14][OH:15])[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22708810HCID 22708810, compound

Product 1

HCID 11264156(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)methanolYield 87.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-20 °C

Procedure

1-(Phenylmethyl)-4-(hydroxymethyl)-pyridinyl chloride (0.87 mol) was dissolved in methanol (2200 ml) and cooled to −20° C. Sodium borohydride (1.75 mol) was added portionwise under a nitrogen atmosphere. The reaction mixture was stirred for 30 minutes and water (200 ml) was added dropwise. The reaction mixture was partially evaporated, water was added and the reaction mixture was extracted with DCM. The organic layer was separated, dried, filtered and evaporated. The residue was purified over silica gel (eluent: DCM), yielding 155 g of 1,2,3,6-tetrahydro-1-(phenylmethyl)-4-pyridinemethanol.

Workup

  1. customThe reaction mixture was partially evaporated
  2. additionwater was added
  3. extractionthe reaction mixture was extracted with DCM
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified over silica gel (eluent: DCM)

Sources & evidence

ORD record
ord-d9b2d47fc4f848cba492954929fc6592
Source dataset
uspto-grants-2012_11
Patent number
US08318742B2

Reaction notes

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