2-(2-Phenylethyl)chromone → 1'-hydroxy-2,3-dihydro-6-fluoro-2-(2-propyl)-spiro-(4H-1-benzopyran-4,3'-pyrrolidine)-2'-one

HRID 2248297Notes

Reaction equation

HRID 2248297 reaction equation
FC1C=CC2OC(CCC)CC(=O)C=2C=1.C([O:23][N:24]1[CH2:28][CH2:27][C:26]2([C:33]3[CH:34]=[C:35]([F:38])[CH:36]=[CH:37][C:32]=3[O:31][CH:30]([CH:39]([CH3:41])[CH3:40])[CH2:29]2)[C:25]1=[O:42])C1C=CC=CC=1.C1(CCC2OC3C=CC=CC=3C(=O)C=2)C=CC=CC=1>>[OH:23][N:24]1[CH2:28][CH2:27][C:26]2([C:33]3[CH:34]=[C:35]([F:38])[CH:36]=[CH:37][C:32]=3[O:31][CH:30]([CH:39]([CH3:40])[CH3:41])[CH2:29]2)[C:25]1=[O:42]

Participants

4

Reactant 3

HCID 4419642-(2-Phenylethyl)chromoneHCID 190944371'-benzyloxy-2,3-dihydro-6-fluoro-2-(2-propyl)-spiro-(4H-1-benzopyran-4,3'-pyrrolidine)-2'oneHCID 190944632,3-dihydro-6-fluoro-2-propyl-4H-1-benzopyran-4-one

Product 1

HCID 190944401'-hydroxy-2,3-dihydro-6-fluoro-2-(2-propyl)-spiro-(4H-1-benzopyran-4,3'-pyrrolidine)-2'-one

Procedure

Prepared from 2,3-dihydro-6-fluoro-2-propyl-4H-1-benzopyran-4-one via the intermediacy of the more polar diastereomer of 1'-benzyloxy-2,3-dihydro-6-fluoro-2-(2-propyl)-spiro-(4H-1-benzopyran-4,3'-pyrrolidine)-2'one (Rf=0.2, 1:1 diethyl ether/hexanes) using the same procedure for preparation of Example 7 from 2,3-dihydro-6-fluoro-2-(2-phenylethyl-4H-1-benzopyran-4-one.

Sources & evidence

ORD record
ord-d940d49c57ed454d8f98320043d5375b
Source dataset
uspto-grants-1991_08
Patent number
US05039672

Reaction notes

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