Diethyl Ether → HCID 23702683, compound

A stirred suspension of (1R)-1-phenylethanaminium (2R,3S)-3-phenyloxirane-2-carboxylate [K. Horada, J. Org. Chem., 31, 1407, 1966] (28.54 g, 0.10 mole) in ethanol (60 mL) and water (15 mL) was treated rapidly with a solution of KOH (9.5 g, 0.17 mole) in ethanol (60 mL). The mixture was stirred at ambient temperature for 20 min, ethyl ether (150 mL) added, the mixture stirred an additional 10 min and the white solid filtered off and washed with ethyl ether. A second crop was obtained by dilution of the filtrate with ethyl ether to 500 mL. Both samples were dried in vacuo. The pH of a small sample of crop 1 in water was 8 to 9 while a sample of crop 2 had pH=14. Crop 2 was thus stirred with 15 mL of absolute ethanol for 15 min, filtered, washed with acetone and dried in vacuo. Crop 1 (16.23 g, 80%) [α]D 25=−146° (c=1.0, H2O) and crop 2 (3.03 g 15%) [α]D 25=−143° (c=1.2, H2O). 1H NMR (300 MHz, DMSO-d6) δ2.97 (d, 1H, J=1.8 Hz), 3.66 (d, 1H, J=1.8 Hz), 7.22-7.35 (m, 5 H). HPLC (Method B): 2.74 min.

1. stirringthe mixture stirred an additional 10 min
2. filtrationthe white solid filtered off
3. washwashed with ethyl ether
4. customA second crop was obtained by dilution of the filtrate with ethyl ether to 500 mL
5. customBoth samples were dried in vacuo
6. stirringCrop 2 was thus stirred with 15 mL of absolute ethanol for 15 min
7. filtrationfiltered
8. washwashed with acetone
9. customdried in vacuo
10. customCrop 1 (16.23 g, 80%) [α]D 25=−146° (c=1.0, H2O) and crop 2 (3.03 g 15%) [α]D 25=−143° (c=1.2, H2O)
11. custom2.74 min.

ORD record

ord-d3dcf180d6534bd29df01fd7c6e32c9b

Source dataset

uspto-grants-2007_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07294622B2