1-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylate → Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

HRID 1727199Notes

Reaction equation

HRID 1727199 reaction equation
[N:1]1([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH:4]([C:7](OCC)=[O:8])[CH2:3][CH2:2]1.[H-].C([Al+]CC(C)C)C(C)C>C1C=CC=CC=1>[OH:8][CH2:7][CH:4]1[CH2:5][CH2:6][N:1]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateYield 46.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of 1-tert-butyl 4-ethyl 1,4-piperidinedicarboxylate (Preparation 49, 12.8 g, 0.05 mol) in benzene (300 ml) under nitrogen was added slowly diisobutyl aluminium hydride (1 M solution, 100 ml, 0.1 mol). The reaction mixture was stirred at room temperature for 3 h before quenching by the addition of water (100 ml) followed by addition of hydrochloric acid (1 M) to adjust to pH 4. The organic layer was separated and the aqueous layer extracted with ethyl acetate. The combined organic extracts were dried (Na2SO4) and concentrated to give an oil. The crude oil was purified by flash chromatography on silica gel eluting with ethyl acetate:dichloromethane (6:4) to give the title compound as an oil (5.0 g, 46%).

Workup

  1. custombefore quenching by the addition of water (100 ml)
  2. additionfollowed by addition of hydrochloric acid (1 M)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated
  7. customto give an oil
  8. customThe crude oil was purified by flash chromatography on silica gel eluting with ethyl acetate:dichloromethane (6:4)

Sources & evidence

ORD record
ord-34a9e9ca2f2f4940900886bef486e6e6
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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