Tert-butyl 3-[1-(3,5-difluorophenyl)-2,2-dimethylpropylidene]azetidine-1-carboxylate → HCID 67066008, compound

HRID 602707Notes

Reaction equation

HRID 602707 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9](=[C:14]2[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15]2)[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[C:6]([F:8])[CH:7]=1.[H][H]>[Pd].C(OCC)(=O)C.CO>[F:8][C:6]1[CH:5]=[C:4]([CH:9]([CH:14]2[CH2:15][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17]2)[C:10]([CH3:11])([CH3:12])[CH3:13])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

6

Reactant 2

HCID 67065934Tert-butyl 3-[1-(3,5-difluorophenyl)-2,2-dimethylpropylidene]azetidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 67066008HCID 67066008, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 720 mg (2.14 mmol) of tert-butyl 3-[1-(3,5-difluorophenyl)-2,2-dimethylpropylidene]azetidine-1-carboxylate and 600 mg of palladium on activated carbon (10%) in 6 mL of ethyl acetate and 5 mL of MeOH was pressurized to 50 psi with hydrogen gas at room temperature for 72 h. The solution was filtered through CELITE and the filtrate was concentrated. The residue was purified by silica gel chromatography with hexanes/ethyl acetate to afford the title compound as a white solid; 1H-NMR (CDCl3) δ 0.88 (s, 9H), 1.43 (s, 9H), 2.69 (d, J=11 Hz, 1H), 3.09-3.18 (m, 21), 3.71 (t, J=8.2 Hz, 1H), 3.81 (m, 1H), 4.12 (t, J=8.5 Hz, 1H), 6.49 (br, 1H), 6.69 (m, 2H);

Workup

  1. filtrationThe solution was filtered through CELITE
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel chromatography with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-9af8a90897204bdf8c269da04e2c7169
Source dataset
uspto-grants-2011_03
Patent number
US07906503B2

Reaction notes

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