Sodium ethoxide → (3R,4R)-1-tert-butyl 3-ethyl 4-((R)-1-phenylethylamino)-piperidine-1,3-dicarboxylate

HRID 723472Notes

Reaction equation

HRID 723472 reaction equation
[C:1]1([C@H:7]([NH:9][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])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC[O-].[Na+]>C(O)C>[C:1]1([C@H:7]([NH:9][C@@H:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[CH2:12][C@H:11]2[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 66952586(3S,4R)-1-tert-butyl 3-ethyl 4-((R)-1-phenylethylamino)-piperidine-1,3-dicarboxylate

Product 1

HCID 11080151(3R,4R)-1-tert-butyl 3-ethyl 4-((R)-1-phenylethylamino)-piperidine-1,3-dicarboxylateYield 41.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 252C (2.90 g, 7.71 mmol) in ethanol (70 mL) was treated with 21% NaOEt in ethanol (7.5 mL). The reaction mixture was heated to 50° C. for three hours, cooled to room temperature, and then concentrated. The resulting oil was taken up in dichloromethane (150 mL), washed with 20% NH4Cl (2×50 mL). The organic layer was dried (Na2SO4) and concentrated to an oil. Purification by flash chromatography (10 to 25% EtOAc/Hexane gradient) on silica gel afforded 1.20 g (yield: 41%) of Compound 252D as an oil.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. washwashed with 20% NH4Cl (2×50 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated to an oil
  6. customPurification by flash chromatography (10 to 25% EtOAc/Hexane gradient) on silica gel

Sources & evidence

ORD record
ord-63092c6756694edd8ac1ef6d95f3ebf2
Source dataset
uspto-grants-2006_11
Patent number
US07141571B2

Reaction notes

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