تفاعل #7774

معادلة التفاعل

( 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

المردود 94.4%

المذيبات

MeOH

water

ظروف التفاعل

المعالجة

1. 1
   workup.WAITAfter 2 h
2. 2
   تركيزthe reaction was concentrated
3. 3
   workup.ADDITIONEtOAc was added
4. 4
   غسيلthe organic layer was washed with H2O, brine
5. 5
   أخرىdried
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated

الإجراء التجريبي

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.

المصدر