4-Benzyl-3-[3-(4-benzyloxy-3-cyclopentyloxyphenyl)-4-nitrobutyryl]-oxazolidin-2-one → 4-(4-Benzyloxy-3-cyclopentyloxyphenyl)pyrrolidin-2-one

HRID 1819338Notes

Reaction equation

C(C1CO[C:10](=O)[N:9]1[C:14](=[O:41])[CH2:15][CH:16]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:23]([O:35][CH:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)[CH:22]=1)C[N+]([O-])=O)C1C=CC=CC=1>CCOC(C)=O.[Ni]>[CH2:28]([O:27][C:24]1[CH:25]=[CH:26][C:21]([CH:16]2[CH2:10][NH:9][C:14](=[O:41])[CH2:15]2)=[CH:22][C:23]=1[O:35][CH:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 50 °C

Procedure

4 g of 4-benzyl-3-[3-(4-benzyloxy-3-cyclopentyloxyphenyl)-4-nitrobutyryl]-oxazolidin-2-one was partially dissolved in 75 mL EtOAc/75 mL EtOH/75 mL dioxane. To this suspension was added a suspension of Raney Ni. The mixture was then flushed three times with H2. The mixture was then stirred under H2 at 50° C. overnight and filtered through celite. Concentration under reduced pressure and purification by column chromatography on silica gel 2.2 g of the desired product. Yield: 88%.

Workup

additionTo this suspension was added
customThe mixture was then flushed three times with H2
filtrationfiltered through celite
concentrationConcentration
customunder reduced pressure and purification by column chromatography on silica gel 2.2 g of the desired product

Sources & evidence

ORD record: ord-c4d30a0df20943e7ade69bdc97624a92
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601742B2

Reaction notes

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