反応 #157673

反応方程式

TBAF

TBAF

alcohol

Tert-butyl (1S)-1-(2-(2-(tert-butyldiphenylsilyloxy)ethyl)cyclopropyl)-3-methylbutylcarbamate

→

title compound

収率 88.0%

Tert-butyl (1S)-1-(2-(2-hydroxyethyl)cyclopropyl)-3-methylbutylcarbamate

収率 88.0%

溶媒

THF

反応条件

後処理

1. 1
   その他at 0° C.
2. 2
   その他reaction after 5 h
3. 3
   その他the reaction mixture was quenched with sat. aq. NH4Cl
4. 4
   workup.ADDITIONdiluted with EtOAc
5. 5
   その他The aqueous phase was separated
6. 6
   抽出extracted with EtOAc
7. 7
   洗浄The combined organic layers were washed with brine
8. 8
   乾燥dried (Na2SO4)
9. 9
   ろ過filtered
10. 10
    濃縮concentrated in vacuo

実験手順

To a solution of the crude TBDPS-protected alcohol 11a (464 mg, 0.742 mmol) in dry THF (6 mL) at 0° C. was added TBAF (1.0M/THF, 0.93 mL, 0.927 mmol), and the reaction mixture was allowed to warm to rt while stirring under N2. Since TLC showed uncomplete reaction after 5 h, 0.75 eq. TBAF (0.56 mL) was added. After 9 h, the reaction mixture was quenched with sat. aq. NH4Cl and diluted with EtOAc. The aqueous phase was separated and extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. Flash chromatography (SiO2, 5:5, hexanes/EtOAc) afforded 177 mg (88%) of the title compound as a colorless oil which solidified upon high vacuum to give a white powder. mp 49.8-50.2° C.; [α]D22−30.8 (c 1.0, DCM); 1H NMR (300 MHz, CDCl3) δ 4.50 (appbd, 1H, J=4.5 Hz), 3.66 (bs, 2H), 2.94 (m, 1H), 2.36 (bs, 1H), 1.82 (bs, 1H), 1.71 (m, 1H), 1.45 (s, 9H), 1.39 (t, 2H, J=7.2 Hz), 1.01 (bs, 2H), 0.90 (dd, 6H, J=10.2, 6.6 Hz), 0.50 (m, 1H), 0.43-0.27 (m, 2H); HRMS (ESI) m/z calcd for C15H29NO3Na 294.2045; found 294.2064.

出典