Water → Tert-butyl 4-(aminomethyl)-4-benzylsulfanylpiperidine-1-carboxylate

HRID 453582Notes

Reaction equation

HRID 453582 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([S:14][C:15]1([CH2:28][N+:29]([O-])=O)[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>C(OCC)C.O1CCCC1.C(OCC)(=O)C>[NH2:29][CH2:28][C:15]1([S:14][CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20]1

Participants

7

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydride2×HCID 57475998Tert-butyl 4-(benzylthio)-4-(nitromethyl)piperidine-1-carboxylate

Product 1

HCID 57475999Tert-butyl 4-(aminomethyl)-4-benzylsulfanylpiperidine-1-carboxylateYield 28.1%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of lithium aluminum hydride (0.4 g) and diethyl ether (20 mL) was added a solution of tert-butyl 4-(benzylthio)-4-(nitromethyl)piperidine-1-carboxylate (1.28 g) in diethyl ether (5 mL) at 0° C. The reaction mixture was heated under reflux for 1 hr. Ethyl acetate was added to decompose excess lithium aluminum hydride, and then water was added. The reaction mixture was diluted with a mixed solvent of tetrahydrofuran and ethyl acetate, and the inorganic salt was removed by filtration. The filtrate was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography to give the title compound (0.33 g, yield 28%) as a colorless oil from a fraction eluted with ethyl acetate-methanol (2:1, volume ratio).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1 hr
  3. customthe inorganic salt was removed by filtration
  4. washThe filtrate was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c751a4213cf74a9391817d1ab0f908bf
Source dataset
uspto-grants-2013_07
Patent number
US08492405B2

Reaction notes

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