Cyclobutanone → HCID 86646589, compound

HRID 1922171Notes

Reaction equation

HRID 1922171 reaction equation
[C:1]1(=O)[CH2:4][CH2:3][CH2:2]1.[C:6]([O:10][C:11]([N:13]1[CH2:17][CH2:16][CH:15]([C:18](=[O:28])[CH2:19]P(OCC)(OCC)=O)[CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].[OH-].[K+]>C(O)C>[C:6]([O:10][C:11]([N:13]1[CH2:17][CH2:16][CH:15]([C:18](=[O:28])[CH:19]=[C:1]2[CH2:4][CH2:3][CH2:2]2)[CH2:14]1)=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 14496CyclobutanoneHCID 14797Potassium HydroxideHCID 86646588HCID 86646588, compound

Product 1

HCID 86646589HCID 86646589, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add cyclobutanone (0.738 mL; 9.89 mmol) to a stirred mixture of 3-(2-(diethoxyphosphoryl)-acetyl)pyrrolidine-1-carboxylic acid tert butyl ester (3.14 g, 8.99 mmol) and potassium hydroxide (656 mg, 11.7 mmol) in ethanol (45 mL) kept under nitrogen at 5° C. Warm to room temperature and stir for 3 hours. Concentrate under reduced pressure and subject the residue to silica gel chromatography, eluting with 20% ethyl acetate in hexanes to afford 0.85 g (36%) of the crude desired compound, which is used in the next step without further purification.

Workup

  1. customkept under nitrogen at 5° C
  2. concentrationConcentrate under reduced pressure
  3. washeluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-09f6ad50eebb49f587d8f5567d40955e
Source dataset
uspto-grants-2012_05
Patent number
US08173821B2

Reaction notes

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