Water → tert-Butyl 4-(benzyloxy)piperidine-1-carboxylate

HRID 861382Notes

Reaction equation

HRID 861382 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C)C=O>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 11694980tert-Butyl 4-(benzyloxy)piperidine-1-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride, 80% dispersion in oil (0.14 g, 4.8 mmoI) was added to a solution of 1-(tert-butoxycarbonyl)-4-hydroxypiperidine (1.0 g, 4.8 mmol) [prepared from 4-hydroxypiperidine and di-tert-butyl dicarbonate] in dimethylformamide (30 ml) and the mixture stirred for 30 minutes. Benzyl bromide (0.68 ml, 5.7 mmol) was added and the reaction mixture stirred overnight. The mixture was poured into water and extracted with dichloromethane. The extracts were washed with water and brine, dried (MgSO4) and the residue after evaporation purified by flash chromatography eluting with 0-20% ethyl acetate in hexane to give 1-(tert-butoxycarbonyl)-4-benzyloxypiperidine (1.1 g, 94% ); δH (CDCl3) 1.39 (9H, s, C(CH3)3), 1.82 (2H, m, piperidinyl. H), 3.04 (2H, m, piperidinyl H), 3.59 (3H, m, piperidinyl H), 4.51 (2H, s, OCH2Ph), 7.24-7.39 (5H, m, PhH).

Workup

  1. stirringthe reaction mixture stirred overnight
  2. extractionextracted with dichloromethane
  3. washThe extracts were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. customthe residue after evaporation
  6. custompurified by flash chromatography
  7. washeluting with 0-20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-9fade1782598479db32b8110c79ae9d2
Source dataset
uspto-grants-1998_02
Patent number
US05714498

Reaction notes

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