Cyclopentadiene → Methyl (1S,3S,4R)-2-((1R)-1-phenylethyl)-2-azabicyclo(2.2.1)hept-5-ene-3-carboxylate

HRID 456773Notes

Reaction equation

HRID 456773 reaction equation
[C:1]1([C@H:7](/[N:9]=[CH:10]\[C:11]([O:13][CH3:14])=[O:12])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(CC(O)=O)(F)F.[CH:23]1[CH2:27][CH:26]=[CH:25][CH:24]=1>FC(F)(F)CO>[C:1]1([C@H:7]([N:9]2[C@H:10]([C:11]([O:13][CH3:14])=[O:12])[C@@H:25]3[CH2:26][C@H:27]2[CH:23]=[CH:24]3)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7612CyclopentadieneHCID 27779723,3,3-Trifluoropropionic acidHCID 178501625HCID 178501625, compound

Product 1

HCID 11780161Methyl (1S,3S,4R)-2-((1R)-1-phenylethyl)-2-azabicyclo(2.2.1)hept-5-ene-3-carboxylate

Reagents, catalysts & solvents 1

HCID 64092,2,2-TrifluoroethanolSolvent

Procedure

To a solution of methyl (2Z)-{[(1R)-1-phenylethyl]imino}acetate obtained in Example 42-1 (238 g) in 2,2,2-trifluoroethanol, was added trifluoromethylacetic acid (95.9 mL) at −10° C. The mixture was then stirred at the same temperature. After 1 hr, cyclopentadiene was added dropwise at −10° C. over 30 minutes.

Sources & evidence

ORD record
ord-7dd52d3492074254a2cb18f041a15926
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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