Trifluoroacetic acid → HCID 66875459, compound

HRID 1666370Notes

Reaction equation

HRID 1666370 reaction equation
O[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH:5]=[C:6]1[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C.FC(F)(F)C(O)=[O:41]>ClCCl>[NH:9]1[CH2:8][CH2:7][C:6](=[C:5]2[CH:2]=[CH:21][CH:20]=[C:19]([O:41][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:4]2[CH3:3])[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 53485958Tert-butyl 4-(3-hydroxybenzylidene)piperidine-1-carboxylate

Product 1

HCID 66875459HCID 66875459, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A slurry of tert-butyl 4-(3-hydroxybenzylidene)piperidine-1-carboxylate (500 mg, 1.73 mmol), phenylboronic acid (418 mg, 3.43 mmol), cupric acetate (314 mg, 1.73 mmol), triethyl amine (1.21 mL 1.8 mmol), and 4 Å powdered sieves (300 mg) in dichloromethane (15 mL) was stirred 18 h at ambient temperature. The reaction mixture was diluted with additional solvent and filtered to remove solid material, washed successively with 1N NaOH and brine, and dried over Na2SO4 to provide a brown oil. This material was purified by column chromatography (1:4 ethyl acetate:heptane) to provide the intermediate Boc-protected material (190 mg, 33%). This material was dissolved in dichloromethane (20 mL) and stirred with trifluoroacetic acid (1 mL) for 3 d at ambient temperature. The reaction was concentrated to a foam that was dissolved in toluene and re-evaporated to give the title compound which was used in the next reaction.

Workup

  1. additionThe reaction mixture was diluted with additional solvent
  2. filtrationfiltered
  3. customto remove solid material
  4. washwashed successively with 1N NaOH and brine
  5. dry with materialdried over Na2SO4
  6. customto provide a brown oil
  7. customThis material was purified by column chromatography (1:4 ethyl acetate:heptane)
  8. customto provide the intermediate Boc-protected material (190 mg, 33%)
  9. concentrationThe reaction was concentrated to a foam that
  10. dissolutionwas dissolved in toluene
  11. customre-evaporated

Sources & evidence

ORD record
ord-fec2317af4c14050b9bcea1530281b3f
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

Loading…