Cyclopentanone → HCID 58506549, compound

HRID 2273870Notes

Reaction equation

[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([C@H:22]2[C@@H:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:26][CH2:25][CH2:24][N:23]2[C:33](=[O:42])[C:34]2[C:39]([CH3:40])=[CH:38][CH:37]=[CH:36][C:35]=2[F:41])=[CH:18][CH:17]=1.[C:43]1(=O)[CH2:47][CH2:46][CH2:45][CH2:44]1>ClC(Cl)C>[CH:43]1([NH:15][C:16]2[CH:21]=[CH:20][C:19]([C@H:22]3[C@@H:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:26][CH2:25][CH2:24][N:23]3[C:33](=[O:42])[C:34]3[C:39]([CH3:40])=[CH:38][CH:37]=[CH:36][C:35]=3[F:41])=[CH:18][CH:17]=2)[CH2:47][CH2:46][CH2:45][CH2:44]1

Participants

Conditions

Temperature: 45 °C

Procedure

Step c) NaBH(OAc)3 (14.12 g, 66.60 mmol) was added to a solution of ethyl (2R,3S)-2-(4-aminophenyl)-1-(2-fluoro-6-methylbenzoyl)piperidine-3-carboxylate (16 g, 41.65 mmol), and cyclopentanone (10.51 g, 125 mmol) in dry dichloroethane (200 mL) at rt. The reaction mixture was heated to 45° C. for 3 h, cooled to rt, quenched with saturated aqueous NaHCO3 solution, extracted with dichloromethane, dried and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, ethyl acetate/hexanes 15-40%) to afford ethyl (2R,3S)-2-[4-(cyclopentylamino)phenyl]-1-(2-fluoro-6-methylbenzoyl)piperidine-3-carboxylate as white solid (17 g, 90%). MS: (ES) m/z 453 (M+H+).

Workup

temperaturecooled to rt
customquenched with saturated aqueous NaHCO3 solution
extractionextracted with dichloromethane
customdried
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (SiO2, ethyl acetate/hexanes 15-40%)

Sources & evidence

ORD record: ord-fc8d7079cfc0404698e1cc26947e3cfa
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126939B2

Reaction notes

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