Trifluoroacetic acid → HCID 118207450, compound

HRID 1507187Notes

Reaction equation

HRID 1507187 reaction equation
O[C:2]1([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([CH:2]2[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 659206591497198-86-3

Product 1

HCID 118207450HCID 118207450, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-hydroxy-3-(4-methoxyphenyl)azetidine-1-carboxylate (1.1 g, 3.9 mmol) in DCM (15 mL) at 0° C. was added triethylsilane (5 mL, 31 mmol) followed by TFA (1 mL, 13.8 mmol). The reaction mixture was allowed to warm to rt and stirred overnight. The mixture was then diluted with a satd. sodium bicarbonate solution and extracted with DCM (100 mL). The organic layer was separated, dried over Na2SO4, filtered, and evaporated under reduced pressure to give a crude product which was purified by silica gel chromatography eluting with 10% ethyl aceate in hexane to give pure tert-butyl 3-(4-methoxyphenyl)azetidine-1-carboxylate (380 mg, 1.37 mmol, 34.8% yield). LCMS (Method 107): (ES-API), m/z 264.0 (M+H) RT=2.128 min; 1H NMR (400 MHz, DMSO-d6) δ 7.31-7.20 (m, 2H), 6.96-6.87 (m, 2H), 4.27-4.17 (m, 2H), 3.82-3.69 (m, 6H), 1.41 (s, 9H).

Workup

  1. additionThe mixture was then diluted with a satd
  2. extractionsodium bicarbonate solution and extracted with DCM (100 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto give a crude product which
  8. customwas purified by silica gel chromatography
  9. washeluting with 10% ethyl aceate in hexane

Sources & evidence

ORD record
ord-b2475c2601d94436a4094bfcc961cf48
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

Loading…