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

HRID 602707노트

반응식

HRID 602707 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

HCID 67066008HCID 67066008, 화합물

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

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);

후처리

  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

출처 및 근거

ORD 기록
ord-9af8a90897204bdf8c269da04e2c7169
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906503B2

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