反応 #48317

反応方程式

tert-butyl (2S,3S)-3-(tert-butyldimethylsilyloxy)-1-(3-fluorophenyl)-4-oxobutan-2-ylcarbamate

(S)-2,2-dimethyl-6-neopentyl-1,2,3,4-tetrahydroquinolin-4-amine

DCM

trimethoxymethane

sodium triacetoxyborohydride

→

title compound

Tert-butyl (2S,3R)-3-(tert-butyldimethylsilyloxy)-4-((S)-2,2-dimethyl-6-neopentyl-1,2,3,4-tetrahydroquinolin-4-ylamino)-1-(3-fluorophenyl)butan-2-ylcarbamate

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   その他quenched with saturated Rochelle's salt
3. 3
   workup.STIRRINGstirred for an additional 20 minutes
4. 4
   workup.ADDITIONfunnel containing DCM and H2O
5. 5
   洗浄The aqueous layer was washed 4× with DCM
6. 6
   洗浄washed 1× with brine
7. 7
   乾燥dried with MgSO4
8. 8
   ろ過filtered
9. 9
   濃縮concentrated

実験手順

To a solution of tert-butyl (2S,3S)-3-(tert-butyldimethylsilyloxy)-1-(3-fluorophenyl)-4-oxobutan-2-ylcarbamate (0.148 g, 0.360 mmol) and (S)-2,2-dimethyl-6-neopentyl-1,2,3,4-tetrahydroquinolin-4-amine (0.0886 g, 0.360 mmol) in DCM (7.19 ml, 0.360 mmol) was added trimethoxymethane (0.394 ml, 3.60 mmol). The resulting solution was stirred for 1 hour at which time, sodium triacetoxyborohydride (0.229 g, 1.08 mmol) was added. The solution was then stirred for 30 minutes, quenched with saturated Rochelle's salt and stirred for an additional 20 minutes. The mixture was transferred to a sep. funnel containing DCM and H2O. The aqueous layer was washed 4× with DCM. The organic layers were combined, washed 1× with brine, dried with MgSO4, filtered and concentrated to afford the title compound. MS m/z: 642 (M+1).

出典