Benzhydrylamine → HCID 14992878, compound

3-Aminobutane-1,2-diol was similarly prepared as described in Tetrahedron: Asymmetry, 1995, 6(9), 2329-2342. Briefly, to a solution of (2S,3S)-trans-3-methyloxirane-2-methyl-4-nitrobenzoate (10.0 g, 42.2 mmol) (Fluka) in dichloromethane (150 mL) under argon, was combined with titanium isopropoxide (25 mL, 84.3 mmol), and stirred for minutes at room temperature. Aminodiphenyl-methane (14.5 mL, 84.4 mmol) was added, and the reaction was stirred at room temperature overnight. A solution of 10% sodium hydroxide in saturated brine was added and the suspension was stirred for 2 hours. The mixture was filtered and extracted with 0.2M hydrochloric acid. The acidic layers were extracted with dichloromethane and discarded. The acidic layer was basified with sodium hydroxide pellets until pH 9, and then extracted into dichloromethane. The layers were separated, and the organic layer was dried over magnesium sulfate, and concentrated in vacuo to give an oil that was purified by flash column chromatography using 2:1 to 1:1 hexanes:ethyl acetate and 2:1 ethyl acetate:hexane as eluants to give 2.6 g of (R,R)-3-(benzhydrylamino)butane-1,2-diol.

1. stirringthe reaction was stirred at room temperature overnight
2. stirringthe suspension was stirred for 2 hours
3. filtrationThe mixture was filtered
4. extractionextracted with 0.2M hydrochloric acid
5. extractionThe acidic layers were extracted with dichloromethane
6. extractionextracted into dichloromethane
7. customThe layers were separated
8. dry with materialthe organic layer was dried over magnesium sulfate
9. concentrationconcentrated in vacuo
10. customto give an oil that
11. customwas purified by flash column chromatography

ORD record

ord-e128dc3a3626413e8009825b1b2d37a3

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06451804B1