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

HRID 37728Notes

Reaction equation

HRID 37728 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-5fdb7b29cd3c48a78d22172e09f3d335
Source dataset
uspto-grants-1995_05
Patent number
US05420363

Reaction notes

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