Tetrahydrofuran → Dimethyl (2s,3s,5s)-5-(allyloxy)-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

HRID 535079Notes

Reaction equation

HRID 535079 reaction equation
C(O[C:5]([O:7][C@@H:8]1[CH2:13][N:12]([C:14]([O:16][CH3:17])=[O:15])[C@H:11]([C:18]([N:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:22][CH2:21]2)=[O:19])[C@@H:10]([C:32]([O:34][CH3:35])=[O:33])[CH2:9]1)=O)C=C.O1CC[CH2:38][CH2:37]1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:5]([O:7][C@@H:8]1[CH2:13][N:12]([C:14]([O:16][CH3:17])=[O:15])[C@H:11]([C:18]([N:20]2[CH2:21][CH2:22][N:23]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:24][CH2:25]2)=[O:19])[C@@H:10]([C:32]([O:34][CH3:35])=[O:33])[CH2:9]1)[CH:37]=[CH2:38]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 67304233Dimethyl (2s,3s,5s)-5-[(allyloxy)carbonyl]oxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

Product 1

HCID 67305361Dimethyl (2s,3s,5s)-5-(allyloxy)-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A mixture of dimethyl (2S,3S,5S)-5-[(allyloxy)carbonyl]oxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate (100 mg, 0.0002 mol) and tetrakis(triphenylphosphine)palladium(0) (24 mg, 0.000020 mol) in tetrahydrofuran (5.00 mL, 0.0616 mol) was refluxed for 2 h. The mixture was concentrated to dry and used directly in next step.

Workup

  1. temperaturewas refluxed for 2 h
  2. concentrationThe mixture was concentrated
  3. customto dry

Sources & evidence

ORD record
ord-ad1cb4e83c5447aba3b5f29862bce51a
Source dataset
uspto-grants-2014_10
Patent number
US08853243B2

Reaction notes

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