Acetic Acid → HCID 131735709, compound

HRID 2200385Notes

Reaction equation

O=[C:2]1[CH2:6][CH2:5][C@@H:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.[F:17][C:18]1[CH:19]=[C:20]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:21]=[CH:22][CH:23]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl>[F:17][C:18]1[CH:19]=[C:20]([N:24]2[CH2:29][CH2:28][N:27]([C@H:2]3[CH2:6][CH2:5][C@@H:4]([C:7]([O:9][CH2:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[O:8])[CH2:3]3)[CH2:26][CH2:25]2)[CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of (R)-benzyl 3-oxocyclopentanecarboxylate (1.5 g, 6.87 mmol), 1-(3-fluorophenyl)piperazine (1.36 g, 7.56 mmol) in 1,2-dichloroethane (25 ml) were added 1-(3-fluorophenyl)piperazine (1.36 g, 7.56 mmol), glacial acetic acid (0.4 ml, 6.87 mmol) and Sodium triacetoxy borohydride (2.18 g, 10.31 mmol). The mixture was stirred at 25° C. for 24 h before removal of the solvent. The residue was treated with saturated sodium bicarbonate, extracted with ethyl acetate and washed with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the crude residue which was purified by column chromatography over silica gel using ethyl acetate in hexane as eluents to obtain the title compound as the major diastereomer (1.2 g, 45.7%).

Workup

extractionextracted with ethyl acetate
washwashed with brine
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customto afford the crude residue which
customwas purified by column chromatography over silica gel

Sources & evidence

ORD record: ord-475dc7ae1aaa44568281e81da3e71082
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359367B2

Reaction notes

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