Nitrogen → [4-(2-Methyl-[1,3]dioxolan-2-yl)-pyridin-2-yl]-methanol

HRID 42777Notes

Reaction equation

HRID 42777 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([CH:15]=[O:16])[CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1.[BH4-].[Na+].O>CO>[CH3:3][C:4]1([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([CH2:15][OH:16])[CH:10]=2)[O:5][CH2:6][CH2:7][O:8]1

Participants

6

Reactant 4

HCID 947NitrogenHCID 962WaterHCID 4311764Sodium borohydrideHCID 866494804-(2-Methyl-[1,3]dioxolan-2-yl)-pyridine-2-carbaldehyde

Product 1

HCID 66929049[4-(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), 4-(2-methyl-[1,3]dioxolan-2-yl)-pyridine-2-carbaldehyde (1100 mg, 5.69 mmol) was dissolved in MeOH (15 mL). NaBH4 (278 mg, 7.05 mmol) was added portionwise at 0° C. and the reaction mixture was stirred at rt for 1 h. Water was added and the mixture extracted with EA (3×30 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a yellow oil. LC-MS-conditions 02: tR=0.41 min; [M+H]+=196.51.

Workup

  1. extractionthe mixture extracted with EA (3×30 mL)
  2. dry with materialextracts were dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-e4ad7d7728f34ccab4c7d3b0c09ff896
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

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