Sodium borohydride → 1-(p-Nitrobenzyloxycarbonyl)-4-hydroxypiperidine

HRID 1252210Notes

Reaction equation

HRID 1252210 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+]>CO.O1CCCC1.O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:13][CH2:14][CH:15]([OH:18])[CH2:16][CH2:17]2)=[O:11])=[CH:19][CH:20]=1)([O-:3])=[O:2]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 13292708(4-Nitrophenyl)methyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 132927091-(p-Nitrobenzyloxycarbonyl)-4-hydroxypiperidine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 1-(p-nitrobenzyloxycarbonyl)-4-piperidone (5.46 g) in methanol (54 ml) and tetrahydrofuran (27 ml) was added sodium borohydride (373 mg), followed by stirring at 0° C. for 10 minutes. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and evaporated to give 1-(p-nitrobenzyloxycarbonyl)-4-hydroxypiperidine.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-c74d4f4b9c614aca92a06654fb514af9
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Reaction notes

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