Methanol → (6-(Benzyloxy)pyridin-3-yl)methanol

HRID 595179Notes

Reaction equation

HRID 595179 reaction equation
[BH4-].[Li+].CO.[CH2:5]([O:12][C:13]1[CH:28]=[CH:27][C:16]([C:17](OCC2C=CC=CC=2)=[O:18])=[CH:15][N:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1COCC1.[Cl-].[NH4+]>[CH2:5]([O:12][C:13]1[N:14]=[CH:15][C:16]([CH2:17][OH:18])=[CH:27][CH:28]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 112756628Benzyl 6-(benzyloxy)pyridine-3-carboxylate

Product 1

HCID 59255139(6-(Benzyloxy)pyridin-3-yl)methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
70 °C

Procedure

Lithium borohydride (517 mg, 23.5 mmol) and MeOH (752 mg, 23.5 mmol) were added to a solution of benzyl 6-(benzyloxy)nicotinate (5 g, 15.7 mmol) in THF (50 mL) under N2 at 0° C. The mixture was stirred at 70° C. for 2 hours. The mixture was diluted with saturated aqueous ammonium chloride solution and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/EtOAc) to afford (6-(benzyloxy)pyridin-3-yl)methanol. MS ESI calc'd. for C13H14NO2 [M+H]+ 216. found 216. 1H NMR (400 MHz, DMSO-d6) δ 8.11 (d, J=2.0 Hz, 1H), 7.69-7.67 (m, 1H), 7.45-7.33 (m, 5H), 6.86 (d, J=8.4 Hz, 1H), 5.35 (s, 2H), 5.23-5.20 (m, 1H), 4.52-4.44 (m, 2H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-72dbe1df4f564bc4b937e4ed665410bf
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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