Реакция #162039

ord-a4656bb8e7d34cb5a8df1b1f89428010

Уравнение реакции

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4CC(OCC(=O)OC(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C
tert-Butyl 2-(cholestan-3-yloxy)acetate
O=C(O)C(F)(F)F
TFA
→
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4CC(OCC(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C
white solid
Выход 78.0%
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4CC(OCC(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C
2-(Cholestan-3-yloxy)acetic acid
Выход 78.0%

Реактанты

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4CC(OCC(=O)OC(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C
tert-Butyl 2-(cholestan-3-yloxy)acetate
O=C(O)C(F)(F)F
TFA

Реагенты

Нет

Растворители

ClCCl
DCM

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    workup.ADDITIONwas added
  2. 2
    ДругоеThe solvent was evaporated
  3. 3
    Другоеthe residue purified
  4. 4
    Другоеbefore being recrystallized from hexane

Методика

tert-Butyl 2-(cholestan-3-yloxy)acetate 129 (634 mg, 1.26 mmol) was taken up in DCM (4 mL) before TFA (1 mL) was added. The solution was stirred at room temperature for 90 mins. The solvent was evaporated and the residue purified using a short silica plug (SiO2: DCM to 100:5 DCM:MeOH) before being recrystallized from hexane to yield 439 mg of the white solid product (78%). 1H nmr (400 MHz, CDCl3) δ: 4.25 (s, 2H, CH2O), 3.37 (m, 1H, CHO), 1.99-0.58 (m, 31H), 0.89 (d, 3H, J=6.6, CH3), 0.85 (d, 3H, J=2.0, CH3), 0.84 (d, 3H, J=1.4, CH3), 0.80 (s, 3H, CH3), 0.64 (s, 3H, CH3).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08828952B2uspto-grants-2014_09