Methanol → Benzyl 3-(hydroxymethyl)piperidine-1-carboxylate

HRID 659619Notes

Reaction equation

HRID 659619 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]1([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:12][CH2:11][CH2:10][CH:9]([C:13](OCC)=[O:14])[CH2:8]1.C(Cl)Cl.CO>C1COCC1.[OH-].[Na+].O>[OH:14][CH2:13][CH:9]1[CH2:10][CH2:11][CH2:12][N:7]([C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])[CH2:8]1

Participants

7

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 17999271Benzyl ethyl piperidine-1,3-dicarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 2776577Benzyl 3-(hydroxymethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 23719242Sodium hydroxide--water (1/1/1)Solvent

Conditions

Temperature
-10 °C

Procedure

A 250-mL 3-necked round-bottomed flask was charged with a solution of LiAlH4 (2.96 g, 77.83 mmol, 2.00 equiv) in THF (150 mL). To this solution was added 1-benzyl 3-ethyl piperidine-1,3-dicarboxylate (11.4 g, 39.16 mmol, 1.00 equiv) in THF (50 mL) drop wise with stirring at −10° C. The resulting mixture was allowed to stir about 1 hour at −10° C. The progress was monitored by TLC (DCM: MeOH=10:1). The resulting solution was diluted with 10 mL of NaOH/H2O. The solids were filtered out. The resulting mixture was concentrated on a rotary evaporator to afford benzyl 3-(hydroxymethyl)piperidine-1-carboxylate as pale yellow oil in (8.94 g, (92%).

Workup

  1. stirringto stir about 1 hour at −10° C
  2. filtrationThe solids were filtered out
  3. concentrationThe resulting mixture was concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-157b080a4d934fb8a3662c53a080f882
Source dataset
uspto-grants-2011_12
Patent number
US08080566B1

Reaction notes

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