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

HRID 1819365Notes

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

Nitro-compound 16 (4 g) was partially dissolved in 75 mL EtOAc/75 mL EtOH/75 mL dioxane, and a suspension of Raney Ni was added. The mixture was flushed with H2 three times. The mixture was stirred under H2 at 50° C. overnight, then filtered through celite. Concentration and chromatography of the residue on silica gel gave 2.2 g of the desired product. Yield: 88%.

Workup

additionwas added
customThe mixture was flushed with H2 three times
filtrationfiltered through celite
concentrationConcentration and chromatography of the residue on silica gel

Sources & evidence

ORD record: ord-9d930608ea504899bbde07e5123ae743
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601742B2

Reaction notes

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