Sodium borohydride → HCID 67422847, compound

HRID 1987315Notes

Reaction equation

HRID 1987315 reaction equation
[CH3:1][C:2]1[C:3]([C:8](=[O:21])[CH2:9][CH2:10][CH2:11][C:12]([C:14]2[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=2)=[O:13])=[N:4][CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+]>CO>[CH3:20][C:19]1[C:14]([CH:12]([OH:13])[CH2:11][CH2:10][CH2:9][CH:8]([C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[OH:21])=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67423670HCID 67423670, compound

Product 1

HCID 67422847HCID 67422847, compoundYield 106.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1,5-bis-(3-methyl-pyridin-2-yl)-pentane-1,5-dione (340 mg, 1.20 mmol) mmol) in MeOH (15 mL) was added NaBH4 (100 mg, 2.65 mmol) and the mixture was stirred at room temperature for 2 h. MeOH was removed in vacuo, water (25 mL) was added to the residue and the mixture was extracted with CH2Cl2 (3 times 25 mL). The organic extracts were dried over mgSO4 and concentrated to give 365 mg (100%) of 1,5-bis-(3-methyl-pyridin-2-yl)-pentane-1,5-diol as a white foam. 1H NMR(CDCl3): δ 1.52-1.81 (m, 6H), 2.33 (s, 6H), 4.69 (dd, 2H, J=7.5, 4.5 Hz), 4.79-4.86 (m, 2H), 7.09-7.14 (m, 2H), 7.43-7.45 (m, 2H), 8.36-8.39 (m, 2H).

Workup

  1. customMeOH was removed in vacuo, water (25 mL)
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with CH2Cl2 (3 times 25 mL)
  4. customThe organic extracts were dried over mgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-79afb73b21d74a7898afc8256542ae40
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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