Ethanol → methyl(3R,4S)-1-[(E)-2-nitro-1-piperidin-1-ylvinyl]-4-[(3R)-3-phenylpyrrolidin-1-yl]carbonylpiperidine-3-carboxylate

HRID 535090Notes

Reaction equation

HRID 535090 reaction equation
CS/[C:3](/[N:8]1[CH2:13][CH2:12][C@H:11]([C:14]([N:16]2[CH2:20][CH2:19][C@H:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17]2)=[O:15])[C@@H:10]([C:27]([O:29][CH3:30])=[O:28])[CH2:9]1)=[CH:4]\[N+:5]([O-:7])=[O:6].C(O)C.[NH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>>[N+:5](/[CH:4]=[C:3](/[N:8]1[CH2:13][CH2:12][C@H:11]([C:14]([N:16]2[CH2:20][CH2:19][C@H:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17]2)=[O:15])[C@@H:10]([C:27]([O:29][CH3:30])=[O:28])[CH2:9]1)\[N:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)([O-:7])=[O:6]

Participants

4

Reactant 3

HCID 702EthanolHCID 8082PiperidineHCID 67304566Methyl (3r,4s)-1-[(z)-1-(methylthio)-2-nitrovinyl]-4-[(3r)-3-phenylpyrrolidin-1-yl]carbonylpiperidine-3-carboxylate

Product 1

HCID 67304657methyl(3R,4S)-1-[(E)-2-nitro-1-piperidin-1-ylvinyl]-4-[(3R)-3-phenylpyrrolidin-1-yl]carbonylpiperidine-3-carboxylateYield 71%

Conditions

Temperature
85 °C

Procedure

To a stirred solution of methyl (3R,4S)-1-[(Z)-1-(methylthio)-2-nitrovinyl]-4-[(3R)-3-phenylpyrrolidin-1-yl]carbonylpiperidine-3-carboxylate (81.0 mg, 0.000187 mol) in ethanol (3.0 mL, 0.051 mol) was added piperidine (92.8 uL, 0.000934 mol). The reaction mixture was heated to reflux (oil bath temperature: 85° C.) for 17 h 45 min. The reaction mixture was concentrated in vacuo. The residue was purified by Combiflash with 0-8% MeOH/CH2Cl2 to give the product as a yellow solid (62 mg, 71% in yield). MS (ESI): (M+H)+=471.1.

Workup

  1. temperatureThe reaction mixture was heated
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe residue was purified by Combiflash with 0-8% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-86d0059da46f4c7b8d0dce17ee575e2e
Source dataset
uspto-grants-2014_10
Patent number
US08853243B2

Reaction notes

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