Sodium ethoxide → 1-(1,1-Dimethylethyl) 3-ethyl 4-oxo-1,3-piperidinedicarboxylate

HRID 2261061Notes

Reaction equation

HRID 2261061 reaction equation
C1([C@H](N[C@@H:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][C@H:11]2[C:23]([O:25][CH2:26][CH3:27])=[O:24])C)C=CC=CC=1.CC[O-:30].[Na+]>CCO>[O:30]=[C:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH:11]1[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 11080151(3R,4R)-1-tert-butyl 3-ethyl 4-((R)-1-phenylethylamino)-piperidine-1,3-dicarboxylate

Product 1

HCID 64208761-(1,1-Dimethylethyl) 3-ethyl 4-oxo-1,3-piperidinedicarboxylateYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 252D (460 mg, 1.22 mmol) and NaOEt (1.25 mL, 21% wt in EtOH) in EtOH (10 ml) was stirred at 50° C. for 3 hrs, then at RT for about 48 hours. The reaction mixture was concentrated in vacuo, followed by the addition of water. The mixture was acidified with 1N HCl to pH 4-5 and the solid was collected by filtration, washed with water and dried to give 300 mg (yield: 71%) of 252A. It had an analytical HPLC retention time=2.065 min. (Chromolith SpeedROD column 4.5×50 mm, 10-90% aqueous methanol containing 0.1% TFA over 4 min, 4 mL/min, monitoring at 220 nm). Mass (M+1)+=349.

Workup

  1. waitat RT for about 48 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionfollowed by the addition of water
  4. filtrationthe solid was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-e329eb1d4cdd49029680cdd7a39f66d7
Source dataset
uspto-grants-2010_12
Patent number
US07846931B2

Reaction notes

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