Cyclobutanone → HCID 57635029, compound

HRID 2111248Notes

Reaction equation

HRID 2111248 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:9])[CH2:6][CH2:7][NH2:8])[CH3:3].[C:10]1(=O)[CH2:13][CH2:12][CH2:11]1.C([O-])(=O)C.[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:2]([O:4][C:5](=[O:9])[CH2:6][CH2:7][NH:8][CH:10]1[CH2:13][CH2:12][CH2:11]1)[CH3:3]

Participants

6

Reactant 4

HCID 14496CyclobutanoneHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 57635029HCID 57635029, compoundYield 18.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 10.4 g (0.067 mole) of beta-alanine ethyl ester hydrochloride and 5.0 g (0.071 mole) of cyclobutanone in 200 mL of dichloromethane was added 6.1 g (0.074 mole) of sodium acetate and 21.5 g (0.101 mole) of sodium triacetoxyborohydride. The mixture was stirred at room temperature for 24 hours and then quenched by the addition of 200 mL of aqueous sodium bicarbonate. After 20 minutes, the organic layer was separated and the aqueous layer was extracted with twice with 50 mL of dichloromethane. The combined organic layers dried over anhydrous magnesium sulfate, filtered, and concentrated. Purification of the residue by silica gel chromatography, eluting with hexanes-ethyl acetate (20:80) gave 2.1 g of 3-cyclobutylamino-propanoic acid ethyl ester.

Workup

  1. customquenched by the addition of 200 mL of aqueous sodium bicarbonate
  2. waitAfter 20 minutes
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with twice with 50 mL of dichloromethane
  5. dry with materialThe combined organic layers dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue by silica gel chromatography
  9. washeluting with hexanes-ethyl acetate (20:80)

Sources & evidence

ORD record
ord-1f671ee22706492ba85c60fa592f7e95
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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