HCID 19094439, compound → HCID 14986550, compound

HRID 2248299Notes

Reaction equation

HRID 2248299 reaction equation
ClC1C(Cl)=CC2O[C@@H](C)C[C@H](C([O-])=O)C=2C=1.C(ON1CCC2(C3C=C(F)C=CC=3OC(C)C2)C1=O)C1C=CC=CC=1.C([O:49][N:50]1[CH2:54][CH2:53][C:52]2([C:59]3[CH:60]=[C:61]([Cl:65])[C:62]([Cl:64])=[CH:63][C:58]=3[O:57][CH:56]([CH3:66])[CH2:55]2)[C:51]1=[O:67])C1C=CC=CC=1>>[OH:49][N:50]1[CH2:54][CH2:53][C:52]2([C:59]3[CH:60]=[C:61]([Cl:65])[C:62]([Cl:64])=[CH:63][C:58]=3[O:57][CH:56]([CH3:66])[CH2:55]2)[C:51]1=[O:67]

Participants

4

Reactant 3

HCID 19094439HCID 19094439, compoundHCID 19094447HCID 19094447, compoundHCID 86744984HCID 86744984, compound

Product 1

HCID 14986550HCID 14986550, compound

Procedure

Prepared from methyl cis and trans 6,7-dichloro-2,3-dihydro-2-methyl-4H-1-benzopyran-4-carboxylate in the same manner as the product of Example 6, part 4 from more polar diastereomer of 1'-benzyloxy-2,3-dihydro-6-fluoro-2-methyl-spiro-(4H-1-benzopyran-4,3'-pyrrolidine)-2'-one, via intermediacy of methyl cis and trans 6,7-dichloro-2,3-dihydro-2-methyl-4-(2-propenyl)-4H-1-benzopyran-4carboxylate (Rf=0.6, 1:1 diethyl ether/hexanes, SiO2), methyl cis and trans 6,7-dichloro-2,3-dihydro-2-methyl-4-(2-benzyloxyaminoethyl)-4H-1-benzopyran-4-carboxylate (Rf=0.4, 1:1 diethyl ether/hexanes, SiO2), and the more polar diasteromer of 1'-benzyloxy-2,3-dihydro-6,7-dichloro-2-methyl-spiro-(4H-1-benzopyran-4,3'-pyrrolidine)-2'one (Rf=0.7, diethyl ether, SiO2).

Sources & evidence

ORD record
ord-ae99df2784c447469c44901b72fcd990
Source dataset
uspto-grants-1991_08
Patent number
US05039672

Reaction notes

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