(E)-tert-butyl 4-methyl-4-((5-oxohex-3-en-1-yl)oxy)piperidine-1-carboxylate → Tert-butyl 4-methyl-4-((5-oxohexyl)oxy)piperidine-1-carboxylate

HRID 921142Notes

Reaction equation

HRID 921142 reaction equation
[CH3:1][C:2]1([O:15][CH2:16][CH2:17]/[CH:18]=[CH:19]/[C:20](=[O:22])[CH3:21])[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>CO.[Pd]>[CH3:1][C:2]1([O:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:22])[CH3:21])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 118307125(E)-tert-butyl 4-methyl-4-((5-oxohex-3-en-1-yl)oxy)piperidine-1-carboxylate

Product 1

HCID 118307169Tert-butyl 4-methyl-4-((5-oxohexyl)oxy)piperidine-1-carboxylateYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (E)-tert-butyl 4-methyl-4-((5-oxohex-3-en-1-yl)oxy)piperidine-1-carboxylate (6.2 g, 19.91 mmol) in MeOH (100 mL) was added 10% Pd/C (2.119 g, 1.991 mmol) and the flask was three times evacuated and released to H2, then left under balloon H2 atmosphere for 5 h. Then, filtered and concentrated to give tert-butyl 4-methyl-4-((5-oxohexyl)oxy)piperidine-1-carboxylate (5.8 g, 18.50 mmol, 93% yield) as colorless oil. 1H NMR (500 MHz, CDCl3) δ 3.77-3.70 (m, 2H), 3.32 (t, J=6.3 Hz, 2H), 3.13 (t, J=11.2 Hz, 2H), 2.48 (t, J=7.3 Hz, 2H), 2.16 (s, 3H), 1.77-1.62 (m, 4H), 1.59-1.53 (m, 2H), 1.48 (s, 9H), 1.45-1.37 (m, 2H), 1.16 (s, 3H). LCMS (M+Na)=336.4.

Workup

  1. customevacuated
  2. filtrationThen, filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8ce42b005bad48babe4af94fa5633d0c
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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