Nitrogen → [6-(2-Methyl-[1,3]dioxolan-2-yl)-pyridin-2-yl]-methanol

HRID 42784Notes

Reaction equation

HRID 42784 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[N:14]=[C:13]([CH:15]=[O:16])[CH:12]=[CH:11][CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1.[BH4-].[Na+].O>CO>[CH3:3][C:4]1([C:9]2[N:14]=[C:13]([CH2:15][OH:16])[CH:12]=[CH:11][CH:10]=2)[O:5][CH2:6][CH2:7][O:8]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 962WaterHCID 4311764Sodium borohydrideHCID 860859206-(2-Methyl-1,3-dioxolan-2-yl)-2-pyridinecarboxaldehyde

Product 1

HCID 66928639[6-(2-Methyl-[1,3]dioxolan-2-yl)-pyridin-2-yl]-methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a ice-cold solution of 6-(2-methyl-[1,3]dioxolan-2-yl)-pyridine-2-carbaldehyde (713 mg, 3.69 mmol) in MeOH (10.0 mL) was added NaBH4 (180 mg, 4.57 mmol in four equal portions). The reaction mixture was then stirred for 1 h at rt. Water was added and the mixture was extracted with EA followed twice with EA-MeOH 9:1. The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to give the title compound as a pale yellow solid. LC-MS-conditions 02: tR=0.46 min; [M+H]+=196.49.

Workup

  1. extractionthe mixture was extracted with EA
  2. dry with materialextracts were dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f2773da8aa684b1994a5186f5f99edc7
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

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