Reaktion #2289863

Reaktionsgleichung

1-methylcyclopropanecarbaldehyde

2-(2,6-dichlorophenyl)-2-((triethylsilyl)oxy)ethanamine

NaBH(OAc)3

→

2-(2,6-dichlorophenyl)-N-((1-methylcyclopropyl)methyl)-2-((triethylsilyl)oxy)ethanamine

Ausbeute 62.8%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethis was quenched with sat. aq. NaHCO3
2. 2
   SonstigeThe layers were separated
3. 3
   ExtraktionThe aqueous layer was extracted with DCM
4. 4
   EinengenThe combined organic layers were concentrated
5. 5
   Sonstigethen purified by prep TLC
6. 6
   Wascheneluted with 5% MeOH/DCM

Vorschrift

To a mixture of 1-methylcyclopropanecarbaldehyde (32.8 mg, 0.390 mmol) in DCM (2.0 ml) was added 2-(2,6-dichlorophenyl)-2-((triethylsilyl)oxy)ethanamine (125 mg, 0.390 mmol) followed by NaBH(OAc)3 (124 mg, 0.585 mmol). After 45 min, this was quenched with sat. aq. NaHCO3. The layers were separated. The aqueous layer was extracted with DCM. The combined organic layers were concentrated then purified by prep TLC eluted with 5% MeOH/DCM to provide 2-(2,6-dichlorophenyl)-N-((1-methylcyclopropyl)methyl)-2-((triethylsilyl)oxy)ethanamine (95 mg, 0.245 mmol, 62.7% yield). 1H NMR (500 MHz, CDCl3) δ 7.28-7.30 (m, 2H), 7.12-7.16 (m, 1H), 5.65 (br. s., 1H), 3.37-3.44 (m, 1H), 2.82-2.90 (m, 1H), 2.69 (br. s., 1H), 2.48 (d, J=11.86 Hz, 1H), 1.60 (br. s., 1H), 1.15 (s, 3H), 0.87-0.92 (m, 9H), 0.51-0.63 (m, 6H), 0.28-0.44 (m, 4H); LCMS (ESI) m/z 388.3 (M+H)+.

Quelle