Chlorobis((1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)borane → (2R,3R,4R,alphaS)-alpha-2-Propenyl-2-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]-ethoxy}tetrahydro-3-phenyl-2H-pyran-4-methanol

HRID 747025Notes

Reaction equation

HRID 747025 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@@H:16]2[C@@H:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C@H:20]([CH:28]=[O:29])[CH2:19][CH2:18][O:17]2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH2:32]([Mg]Br)[CH:33]=[CH2:34].ClB([C@@H]1C[C@@H]2C[C@@H](C2(C)C)[C@H]1C)[C@@H]1C[C@@H]2C[C@@H](C2(C)C)[C@H]1C>>[CH2:34]([C@@H:28]([C@@H:20]1[CH2:19][CH2:18][O:17][C@H:16]([O:15][C@@H:13]([C:5]2[CH:4]=[C:3]([C:2]([F:30])([F:1])[F:31])[CH:8]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:6]=2)[CH3:14])[C@H:21]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[OH:29])[CH:33]=[CH2:32]

Participants

4

Reactant 3

HCID 11131038Chlorobis((1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)boraneHCID 86601738(2R,3R,4R)-2-[(1R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy]-3-phenyl-tetrahydropyran-4-carbaldehydeHCID 178455850HCID 178455850, compound

Product 1

HCID 86606918(2R,3R,4R,alphaS)-alpha-2-Propenyl-2-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]-ethoxy}tetrahydro-3-phenyl-2H-pyran-4-methanol

Procedure

Prepared from (2R,3R,4R)-2-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-tetrahydro-3-phenyl-2H-pyran-4-carboxaldehyde (WO 00/56727A1), allylmagnesium bromide and chlorobis[(1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]borane according to the method of Description 31.

Sources & evidence

ORD record
ord-95dc660321d24c079cfddb4b416721d5
Source dataset
uspto-grants-2008_07
Patent number
US07393858B2

Reaction notes

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