1,8-Diazabicyclo(5.4.0)undec-7-ene → ethyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(7-cyano-2-naphthyl)acrylate

HRID 53961Notes

Reaction equation

HRID 53961 reaction equation
[Br-].[C:2]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([CH2:14][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:11]2)=[CH:6][CH:5]=1)#[N:3].[C:34]([O:38][C:39]([N:41]1[CH2:45][CH2:44][C@H:43]([O:46][C:47]2[CH:52]=[CH:51][C:50]([C:53](=O)[C:54]([O:56][CH2:57][CH3:58])=[O:55])=[CH:49][CH:48]=2)[CH2:42]1)=[O:40])([CH3:37])([CH3:36])[CH3:35].C1CCN2C(=NCCC2)CC1.CCCCCC.C(OCC)(=O)C>O1CCCC1.C(O)C>[C:34]([O:38][C:39]([N:41]1[CH2:45][CH2:44][C@H:43]([O:46][C:47]2[CH:48]=[CH:49][C:50]([C:53](=[CH:14][C:10]3[CH:9]=[CH:8][C:7]4[C:12](=[CH:13][C:4]([C:2]#[N:3])=[CH:5][CH:6]=4)[CH:11]=3)[C:54]([O:56][CH2:57][CH3:58])=[O:55])=[CH:51][CH:52]=2)[CH2:42]1)=[O:40])([CH3:37])([CH3:36])[CH3:35]

Participants

7

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 9936048(7-Cyano-2-naphthyl)methyltriphenylphosphonium bromideHCID 10316641Ethyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-2-oxoacetateHCID 21226206Ethyl acetate hexane

Product 1

HCID 57005545ethyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(7-cyano-2-naphthyl)acrylateYield 85.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

8.40 g of (7-cyano-2-naphthyl)methyltriphenylphosphoniumbromide and 5.0 g of ethyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-2-oxoacetate were suspended in a mixture of 100 ml of tetrahydrofuran and 100 ml of ethanol. With stirring, to the resulting suspension was added 2.51 g of 1,8-diazabicyclo[5.4.0]-7-undecene, followed by stirring for 3 hours at room temperature. After distilling off the solvent, the residue thus obtained was subjected to silica gel column chromatography using a n-hexane/ethyl acetate mixture as an elution solvent, thereby obtaining 6.06 g of ethyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(7-cyano-2-naphthyl)acrylate as a mixture of E and Z forms. A portion of the thus obtained compound was separated into E and Z forms.

Workup

  1. stirringby stirring for 3 hours at room temperature
  2. distillationAfter distilling off the solvent
  3. customthe residue thus obtained

Sources & evidence

ORD record
ord-fa242b898191430a8c61beb93bbd339f
Source dataset
uspto-grants-1997_04
Patent number
US05620991

Reaction notes

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