Cyclopentanone → (Rac)-3-cyclopentylamino-2-methyl-propanoic acid ethyl ester

HRID 2111246Notes

Reaction equation

HRID 2111246 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:10])[CH:6]([CH3:9])[CH2:7][NH2:8])[CH3:3].[C:11]1(=O)[CH2:15][CH2:14][CH2:13][CH2:12]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:10])[CH:6]([CH3:9])[CH2:7][NH:8][CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[CH3:3]

Participants

6

Reactant 4

HCID 8452CyclopentanoneHCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 19611788Ethyl 3-amino-2-methylpropanoate hydrochloride

Product 1

HCID 57635021(Rac)-3-cyclopentylamino-2-methyl-propanoic acid ethyl esterYield 47.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (rac)-3-amino-2-methylpropanoic acid ethyl ester hydrochloride (prepared from 3.09 g, 0.030 mole of (rac)-3-amino-2-methylpropanoic acid, thionyl chloride and ethanol) and 2.8 mL (0.0315 mole) of cyclopentanone and 100 mL of dichloromethane was added 5.4 g (0.066 mole) of sodium acetate and 9.54 g (0.045 mole) of sodium triacetoxyborohydride. The mixture was stirred at ambient temperature for 3 hrs and then quenched by the addition of 50 mL of 10% sodium bicarbonate solution. The aqueous layer was extracted with twice with 100 mL of dichloromethane, and the combined dichloromethane layers dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with dichloromethane-methanol (100:0-95:5 gradient) to give 2.86 g of (rac)-3-cyclopentylamino-2-methyl-propanoic acid ethyl ester.

Workup

  1. customquenched by the addition of 50 mL of 10% sodium bicarbonate solution
  2. extractionThe aqueous layer was extracted with twice with 100 mL of dichloromethane
  3. dry with materialthe combined dichloromethane layers dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with dichloromethane-methanol (100:0-95:5 gradient)

Sources & evidence

ORD record
ord-794bf058da2b47aba399ccfc06843b14
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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