Benzaldehyde → HCID 69818787, compound

A suspension of (2S)-2-amino-3-(4-nitrophenyl)-1-propanol (5.89 g) and benzaldehyde (3.39 g) in dichloromethane (59 ml) was stirred at room temperature for 2.5 hours. The mixture was evaporated, and the residual solid was suspended in ethanol (47 ml)-dichloromethane (11.8 ml). Sodium borohydride (1.25 g) was slowly added to the suspension, and the mixture was stirred at room temperature for 5 hours. The mixture was poured onto water (47 ml) and stirred at room temperature for 15 minutes. The precipitate formed was collected by filtration, washed with water, and dried in vacuo. The crude product was recrystallized from ethanol to give (2S)-2-(benzylamino)-3-(4-nitrophenyl)-1-propanol (5.18 g) as a pale yellow powder. The filtrates obtained above were combined, concentrated, and partitioned between chloroform and water. The organic layer was separated, washed successively with water and brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated and the residue was purified by column chromatography (silica gel, chloroform/methanol) to give the additional amount of product (2.78 g) as a white powder.

1. customThe mixture was evaporated
2. additionSodium borohydride (1.25 g) was slowly added to the suspension
3. stirringthe mixture was stirred at room temperature for 5 hours
4. additionThe mixture was poured onto water (47 ml)
5. stirringstirred at room temperature for 15 minutes
6. customThe precipitate formed
7. filtrationwas collected by filtration
8. washwashed with water
9. customdried in vacuo
10. customThe crude product was recrystallized from ethanol

ORD record

ord-e0552923bb6e492387c8bb994485b02e

Source dataset

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06826033B2