Triacetoxyborohydride → 1-Cycloheptyl-4-{[(2-fluorophenyl)(methyl)amino]methyl}-3,3-dimethylpyrrolidin-2-one

HRID 16209

반응식

HRID 16209 반응식
[CH:1]1([N:8]2[C:12](=[O:13])[C:11]([CH3:15])([CH3:14])[CH:10]([CH:16]=O)[CH2:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[NH:21][CH3:22].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C>O1CCCC1>[CH:1]1([N:8]2[CH2:9][CH:10]([CH2:16][N:21]([C:20]3[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=3[F:18])[CH3:22])[C:11]([CH3:15])([CH3:14])[C:12]2=[O:13])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 2724942TriacetoxyborohydrideHCID 27590102-Fluoro-N-methylanilineHCID 870923081-Cycloheptyl-4,4-dimethyl-5-oxo-pyrrolidine-3-carbaldehyde

생성물 1

HCID 248899041-Cycloheptyl-4-{[(2-fluorophenyl)(methyl)amino]methyl}-3,3-dimethylpyrrolidin-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of Example 4A (30 mg, 0.12 mmoles), 2-fluoro-N-methylaniline (19 mg, 0.15 mmoles) MP-triacetoxyborohydride (137 mg, 0.3 mmoles) in tetrahydrofuran (1.25 mL) was stirred for twelve hours. The reaction was filtered and solvent evaporated in vacuo. The crude reaction mixture was purified by preparative reverse phase HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 um particle size) using a gradient of 20% to 100% acetonitrile:water (0.1% trifluoroacetic acid) over eighteen minutes at a flow rate of 40 mL/minute to provide the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 6.90-7.10 (m, 4H), 4.01-4.13 (m, 1H), 3.32 (dd, J=9.88, 7.50 Hz, 1H), 3.11-3.21 (m, 2H), 3.09 (t, J=9.36 Hz, 1H), 2.83 (s, 3H), 2.17-2.27 (m, 1H), 1.59-1.70 (m, 6H), 1.45-1.57 (m, 6H), 1.16 (s, 3H), 0.95 (s, 3H). MS (APCI+) m/z 347.2 (M+H)+.

후처리

  1. filtrationThe reaction was filtered
  2. customsolvent evaporated in vacuo
  3. customThe crude reaction mixture
  4. customwas purified by preparative reverse phase HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 um particle size)

출처 및 근거

ORD 기록
ord-31ee6aaf27d54276a8f6358ec7884873
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737137B2

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