Dimethyl Sulfide → HCID 86301485, 화합물

HRID 1748391노트

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HRID 1748391 반응식
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][O:7][C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([C:18](=[O:20])[CH3:19])[CH:14]=[N:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@H]2N1CCC2.CSC>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][O:7][C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([C@@H:18]([OH:20])[CH3:19])[CH:14]=[N:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 1068Dimethyl SulfideHCID 2734713(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaboroleHCID 86301334HCID 86301334, 화합물

생성물 1

HCID 86301485HCID 86301485, 화합물수율 17.2%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
-20 °C

실험 절차

To a cooled solution, −78° C., of 1-(7-((4-fluorobenzyl)oxy)quinolin-3-yl)ethanone (Example 42, 52 mg, 0.176 mmol) in toluene was added (S)-(−)-2-methyl-CBS-oxazaborolidine (97 mg, 0.352 mmol) followed by BH3.DMS (2 M in THF, 0.176 mL, 0.352 mmol). The reaction was warmed to −20° C. and stirred for 3 h before being quenched with MeOH. The reaction was warmed to ambient temperature and sat. NaHCO3 (aq.) solution was added. The aqueous layer was extracted with EtOAc and the combined organic fractions were washed with brine and concentrated under reduced pressure onto silica. Purification (FCC, SiO2, 0-5%, MeOH/DCM) afforded the title compound as a white solid (9 mg, 17%). 1H NMR (400 MHz, DMSO-d6) δ 8.85 (d, J=2.3 Hz, 1H), 8.20 (d, J=2.0 Hz, 1H), 7.93 (d, J=9.0 Hz, 1H), 7.61 (dd, J=5.5, 8.6 Hz, 2H), 7.51 (d, J=2.3 Hz, 1H), 7.33 (dd, J=2.5, 8.8 Hz, 1H), 7.28 (t, J=9.0 Hz, 2H), 5.44 (d, J=4.3 Hz, 1H), 5.29 (s, 2H), 5.01-4.91 (m, 1H), 1.47 (d, J=6.7 Hz, 3H). [M+H]=298.2.

후처리

  1. custombefore being quenched with MeOH
  2. temperatureThe reaction was warmed to ambient temperature
  3. additionsat. NaHCO3 (aq.) solution was added
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washthe combined organic fractions were washed with brine
  6. concentrationconcentrated under reduced pressure onto silica
  7. customPurification (FCC, SiO2, 0-5%, MeOH/DCM)

출처 및 근거

ORD 기록
ord-698c523bf215491095bd8da86d4bb12a
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150572B2

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