Tert-butyl 4-(1-ethoxy-1-oxopropan-2-ylidene)piperidine-1-carboxylate → Ethyl 1-[(1,1-dimethylethoxy)carbonyl]-α-methyl-4-piperidineacetate

HRID 1804839Notes

Reaction equation

HRID 1804839 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5](=[C:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)[CH3:6])[CH3:2]>CCO>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([CH:7]1[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[CH2:11][CH2:12]1)[CH3:6])[CH3:2]

Participants

3

Reactant 1

HCID 59464295Tert-butyl 4-(1-ethoxy-1-oxopropan-2-ylidene)piperidine-1-carboxylate

Product 1

HCID 18670567Ethyl 1-[(1,1-dimethylethoxy)carbonyl]-α-methyl-4-piperidineacetateYield 47.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Step 1 above was dissolved in absolute EtOH (10 mL) and hydrogenated over Pt2O (150 mg) for 14 h. After this time, the reaction was filtered to remove the catalyst and concentrated on a rotary evaporator to give tert-butyl 4-(1-ethoxy-1-oxopropan-2-yl)piperidine-1-carboxylate (1.5 g, 5.26 mmol, 47.6% yield, 2 steps) as a colorless liquid. 1H-NMR (400 MHz, CDCl3) δ ppm 4.03-4.15 (4 H, m), 2.63 (2 H, t, J=11.58 Hz), 2.18-2.26 (1 H, m, J=7.18, 7.18, 7.18, 7.18 Hz), 1.59-1.70 (2 H, m), 1.47-1.57 (1 H, m), 1.41 (9 H, s), 1.22 (3 H, t, J=7.18 Hz), 1.24-1.18 (m, 2 H), 1.14 (1 H, dd, J=13.22, 4.41 Hz), 1.09 (3 H, d, J=7.05 Hz).

Workup

  1. filtrationAfter this time, the reaction was filtered
  2. customto remove the catalyst
  3. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-7cb3121a449b40c59a6f55bdb5fc72f9
Source dataset
uspto-grants-2013_01
Patent number
US08354432B2

Reaction notes

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