Sodium borohydride → Tert-butyl 4-(6-hydroxymethyl-pyridin-3-yl)-piperazine-1-carboxylate

HRID 2100666Notes

Reaction equation

HRID 2100666 reaction equation
[CH:1]([C:3]1[N:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+]>C1COCC1>[OH:2][CH2:1][C:3]1[N:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58181229tert-Butyl 4-(6-formylpyridin-3-yl)piperazine-1-carboxylate

Product 1

HCID 68814347Tert-butyl 4-(6-hydroxymethyl-pyridin-3-yl)-piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-(6-formyl-pyridin-3-yl)-piperazine-1-carboxylate (0.39 mmol) in THF (10 mL) is added NaBH4 (2.72 mmol) and the reaction mixture is stirred at room temperature for 1 hour. After it is cooled to 0° C., the reaction mixture is slowly mixed with ice cold water (5 mL) and then partitioned between saturated Na2CO3 solution and 10% MeOH in EtOAc. The aqueous phase is extracted with 10% MeOH in EtOAc. The combined organic extracts are washed with saturated aqueous NaCl and dried over Na2SO4. After concentration, the residue is purified by silica gel chromatography (100/10/1 EtOAc/MeOH/Et3N) to give tert-butyl 4-(6-hydroxymethyl-pyridin-3-yl)-piperazine-1-carboxylate.

Workup

  1. temperatureAfter it is cooled to 0° C.
  2. custompartitioned between saturated Na2CO3 solution and 10% MeOH in EtOAc
  3. extractionThe aqueous phase is extracted with 10% MeOH in EtOAc
  4. washThe combined organic extracts are washed with saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentration
  7. customthe residue is purified by silica gel chromatography (100/10/1 EtOAc/MeOH/Et3N)

Sources & evidence

ORD record
ord-818e190f841f484d8adfbc81b6b3449f
Source dataset
uspto-grants-2009_08
Patent number
US07572811B2

Reaction notes

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