反応 #317203

反応方程式

5-bromoindan-1-one

4-tert-butylcyclohexyl amine

Sodium borohydride

→

(5-Bromo-2,3-dihydro-1H-inden-1-yl)(trans-4-tert-butylcyclohexyl)amine

溶媒

ethanol

反応条件

後処理

1. 1
   workup.STIRRINGthe resulting mixture was stirred for an additional 8 h at room temperature
2. 2
   その他The reaction was quenched
3. 3
   workup.ADDITIONby pouring into aqueous ammonia (2N, 300 mL)
4. 4
   ろ過The resulting inorganic precipitate was filtered off
5. 5
   洗浄washed with dichloromethane (150 mL)
6. 6
   その他The organic layer was separated
7. 7
   抽出the remaining aqueous layer was extracted once with dichloromethane (150 mL)
8. 8
   乾燥The combined organic extracts were dried over Na2SO4
9. 9
   ろ過filtered
10. 10
    濃縮concentrated

実験手順

A mixture of 5-bromoindan-1-one (6.33 g, 30.0 mmol), titanium (IV) isopropoxide (17.8 mL, 60.0 mmol), 4-tert-butylcyclohexyl amine (9.32 g, 60.0 mmol) in absolute ethanol (200 mL) was stirred under nitrogen at room temperature for 12 h. Sodium borohydride (1.70 g, 45.0 mmol) was then added and the resulting mixture was stirred for an additional 8 h at room temperature. The reaction was quenched by pouring into aqueous ammonia (2N, 300 mL). The resulting inorganic precipitate was filtered off and washed with dichloromethane (150 mL). The organic layer was separated and the remaining aqueous layer was extracted once with dichloromethane (150 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated. Chromatography (10% to 20% EtOAc in Hexane) afforded (5-Bromo-2,3-dihydro-1H-inden-1-yl)(trans-4-tert-butylcyclohexyl)amine and the corresponding cis product (less polar). HPLC/MS: m/z=350.1 (M+1), Rt=3.01 min.

出典