Dimethyl Sulfide → HCID 86301485、化合物

HRID 1748391ノート

反応式

HRID 1748391 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 86301485HCID 86301485、化合物収率 17.2%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
-20 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-698c523bf215491095bd8da86d4bb12a
出典データセット
uspto-grants-2015_10
特許番号
US09150572B2

反応ノート

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