Methanol → methyl (S)-7-(4-fluorophenyl)-7-hydroxyheptanoate

HRID 37728

반응식

HRID 37728 반응식
C1(C2(C3C=CC=CC=3)OB(C)N3CCC[C@H]23)C=CC=CC=1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:29](=[O:39])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])=[CH:25][CH:24]=1.CO>O1CCCC1>[F:22][C:23]1[CH:24]=[CH:25][C:26]([C@@H:29]([OH:39])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])=[CH:27][CH:28]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 9838490(R)-2-Methyl-CBS-oxazaborolidineHCID 19936161Methyl 7-(4-fluorophenyl)-7-oxoheptanoate

생성물 1

HCID 10562892methyl (S)-7-(4-fluorophenyl)-7-hydroxyheptanoate수율 98.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매4회

실험 절차

To a solution of (R)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c] [1,3,2]oxazaborole (1.1 g) in tetrahydrofuran (20 ml) was added at 0° C. 1M tetrahydrofuran solution of boranetetrahydrofuran complex (4 ml). To this solution were added dropwise a solution of methyl 7-(4-fluorophenyl)-7-oxoheptanoate (10.0 g, 39.6 mmol) in tetrahydrofuran (20 ml) and 1M tetrahydrofuran solution of boranetetrahydrofuran complex (20 ml), simultaneously, taking 25 minutes. The mixture was stirred for 30 minutes at the same temperature range, to which was added methanol (20 ml), followed by stirring for 30 minutes at room temperature. The solvent was distilled off under reduced pressure, and the residue was subjected to a silica gel column chromatography to give methyl (S)-7-(4-fluorophenyl)-7-hydroxyheptanoate (9.91 g). Physico-chemical properties and spectral data of this product are shown in [Table 7]. Likewise, Compound 1-2 was prepared.

후처리

  1. stirringby stirring for 30 minutes at room temperature
  2. distillationThe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-5fdb7b29cd3c48a78d22172e09f3d335
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420363

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