Sodium borohydride → HCID 22324721, compound

HRID 496422Notes

Reaction equation

HRID 496422 reaction equation
[O:1]=[C:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[CH2:3][O:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1.[BH4-].[Na+]>CO>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH:2]([OH:1])[CH2:3][O:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22324729HCID 22324729, compound

Product 1

HCID 22324721HCID 22324721, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-oxo-2-pyridin-2-yl-O-(tetrahydro-2H-pyran-2-yl)ethanol (1.15 g, 0.00520 mol) in methanol at 0° C. is added sodium borohydride (0.195 g, 0.00515 mol) in portions. The reaction is stirred for 2.5 hours and rotary evaporated to dryness. The residue is dissolved in ethyl ether, washed with brine (3×), dried (Na2SO4), and rotary evaporated. The residue is purified by chromatography on silica gel (50 g, 230-400 mesh), eluting with hexanes-ethyl acetate (1:1) to give 0.84 g of (±)-1-pyridin-2-yl-2-(tetrahydro-2H-pyran-2-yloxy)-ethanol as a pale yellow oil. MS-APCI m/z 224 [M−H]+. 4. (±)-6-(2-Tetrahydro-2H-1-pyran-2-yloxy-1-(2-pyridyl)ethoxy)-5-(2-phenylethyl)-2,3,4-trihydronaphthalen-1-one

Workup

  1. customrotary evaporated to dryness
  2. dissolutionThe residue is dissolved in ethyl ether
  3. washwashed with brine (3×)
  4. dry with materialdried (Na2SO4), and rotary evaporated
  5. customThe residue is purified by chromatography on silica gel (50 g, 230-400 mesh)
  6. washeluting with hexanes-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-749cd521a4784c74811ec9261f0a81eb
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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