Diethyl Ether → HCID 178461842, compound

To an ice cold solution of (R)-1-phenylethanamine (3.11 g, 25.7 mmol) and triethylamine (17.9 mL, 128 mmol) in dichloromethane (60 mL) was added dropwise neat titanium tetrachloride (10.7 mL, 10.7 mmol) to afford a light brown mixture. The cold bath was removed and 2,2-dimethylcyclopentanone (2.68 mL, 21.4 mmol) was added and the resulting mixture was allowed to stir at rt for ˜16 h. To this mixture was added 75 mL of diethyl ether and the resulting mixture was stirred at rt for 15 min then filtered thru a pad of Celite to remove the solids. The solids were rinsed with additional ether (30 mL×2) and the resulting clear yellow filtrate was concentrated on a rotovap to afford 4.86 g (quantitative) of the title compound as a yellow liquid. HPLC (condition B): retention time=1.58 min. LCMS (condition E): m/z 216+ve.

1. customto afford a light brown mixture
2. customThe cold bath was removed
3. stirringthe resulting mixture was stirred at rt for 15 min
4. filtrationthen filtered
5. customto remove the solids
6. washThe solids were rinsed with additional ether (30 mL×2)
7. concentrationthe resulting clear yellow filtrate was concentrated on a rotovap

ORD record

ord-05901c2193bc4722a981c64e6418db1f

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921368B2