Lithium borohydride → 1-Boc-4-(hydroxymethyl)-4-methylpiperidine

HRID 1038823Notes

Reaction equation

HRID 1038823 reaction equation
[CH3:1][C:2]1([C:15](OCC)=[O:16])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[Li+].[BH4-]>C1COCC1.C(O)C.O>[OH:16][CH2:15][C:2]1([CH3:1])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1

Participants

6

Reactant 2

HCID 4148881Lithium borohydrideHCID 162182761-tert-Butyl 4-ethyl 4-methylpiperidine-1,4-dicarboxylate

Product 1

HCID 232828431-Boc-4-(hydroxymethyl)-4-methylpiperidineYield 80%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-tert-butyl 4-ethyl 4-methylpiperidine-1,4-dicarboxylate (0.10 g, 0.37 mmol) in THF (10 mL) and ethanol (20 mL) was added LiBH4 (0.032 g, 1.5 mmol). The mixture was stirred for about 8 h at rt. The mixture was diluted with water (20 mL) and extracted with EtOAc (3×20 mL). The EtOAc extracts were combined, dried over anhydrous Na2SO4, and concentrated in vacuo to give tert-butyl 4-(hydroxymethyl)-4-methylpiperidine-1-carboxylate (0.067 g, 80%): LC/MS (Table 2, Method i) Rt=0.29 min; MS m/z: 130 (M-Boc+H)+.

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2010665652c7471e81322fa3aa62a370
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

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