Reaction #162039

ord-a4656bb8e7d34cb5a8df1b1f89428010

Reaction equation

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
Yield 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
Yield 78.0%

Reactants

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

Reagents

None

Solvents

ClCCl
DCM

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONwas added
  2. 2
    OtherThe solvent was evaporated
  3. 3
    Otherthe residue purified
  4. 4
    Otherbefore being recrystallized from hexane

Procedure

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).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08828952B2uspto-grants-2014_09