Iodoethane → (Rac)-2-cyclopentylaminomethyl-butanoic acid ethyl ester

To a mixture of 1.0 g (0.0054 mole) of 3-cyclopentylamino-propanoic acid ethyl ester, 0.842 g (0.00542 mole) of iodoethane and 15 mL of dry tetrahydrofuran, at −78 degrees, was added 11.4 mL (0.0114 mole) of a 1M solution of lithium bis(trimethylsilyl)amide in hexanes over 5 minutes. The mixture was stirred for one hour at −78 degrees, then the cooling bath was removed and the mixture stirred overnight at room temperature, and then poured into ice water containing 5 mL of 1M sodium hydroxide solution. The mixture was extracted with ether, and the ether extract washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 0.5125 g of (rac)-2-cyclopentylaminomethyl-butanoic acid ethyl ester, which was used without further purification in subsequent steps.

1. customthe cooling bath was removed
2. stirringthe mixture stirred overnight at room temperature
3. additionpoured into ice water containing 5 mL of 1M sodium hydroxide solution
4. extractionThe mixture was extracted with ether
5. extractionthe ether extract
6. washwashed with brine
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORD record

ord-bedeb39e31ec4b00b2498c46e4ff2d53

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07517873B2