Réaction #7774

Équation de réaction

( 118ba )

[(1S,2R,4R)-2-(4-bromo-benzenesulfonylmethyl)-4-isopropylamino-cyclohexyl]-carbamic acid benzyl ester

formaldehyde

NaBH3CN

→

[(1S,2R,4R)-2-(4-Bromo-benzenesulfonylmethyl)-4-(isopropyl-methyl-amino)-cyclohexyl]-carbamic acid benzyl ester

Rendement 94.4%

Solvants

MeOH

water

Conditions de réaction

Traitement

1. 1
   workup.WAITAfter 2 h
2. 2
   Concentrationthe reaction was concentrated
3. 3
   workup.ADDITIONEtOAc was added
4. 4
   Lavagethe organic layer was washed with H2O, brine
5. 5
   Autredried
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated

Mode opératoire

The above derivative (118ba) (1.96 g) was dissolved in MeOH (15 ml) prior to the addition of 37% formaldehyde in water (1.41 ml). After 10 min, NaBH3CN (708 mg) was added. After 2 h, the reaction was concentrated. EtOAc was added and the organic layer was washed with H2O, brine, dried, filtered, and concentrated to give [(1S,2R,4R)-2-(4-Bromo-benzenesulfonylmethyl)-4-(isopropyl-methyl-amino)-cyclohexyl]-carbamic acid benzyl ester (1.9 g), MS found: (M+H)+=539.3.

Source