2-Norbornene → 8,9-Di(tetrahydropyranyloxycarbonyl)tetracyclo[4.4.0.12,5.17,10]dodeca-3-ene

HRID 353415Notes

Reaction equation

HRID 353415 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)C=C2.C(O[C:13]([CH:15]1[CH2:20][CH:19]2[CH2:21]C1C=C2)=[O:14])(C)(C)C.C([O:26][C:27]([CH:29]1[CH:34]([C:35]([O:37]C(C)(C)C)=[O:36])[CH:33]2[CH2:42][CH:30]1[CH:31]=[CH:32]2)=[O:28])(C)(C)C.C(OC(COC([CH:54]1[CH:59]([C:60]([O:62][CH2:63][C:64](OC(C)(C)C)=O)=O)C2CC1C=C2)=O)=O)(C)(C)C.C(OC(C1CC2CC1C1C2C2CC1C=C2)=O)(C)(C)C.C12C3CC(CC3)C1C1CC2C=C1>>[O:62]1[CH2:60][CH2:59][CH2:54][CH2:64][CH:63]1[O:26][C:27]([CH:29]1[CH:34]([C:35]([O:37][CH:21]2[CH2:19][CH2:20][CH2:15][CH2:13][O:14]2)=[O:36])[CH:33]2[CH2:42][CH:30]1[CH:31]1[CH:32]2[CH:6]2[CH2:5][CH:4]1[CH:7]=[CH:1]2)=[O:28]

Participants

7

Reactant 6

HCID 103522-NorborneneHCID 136844Tetracyclododecene2×HCID 155389668-t-Butoxycarbonyltetracyclo[4.4.0.12,5.17,10]dodeca-3-eneHCID 15607334Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 1,1-dimethylethyl esterHCID 219223175,6-Di(t-butoxycarbonyl)norborneneHCID 220238465,6-Di(t-butoxycarbonylmethoxycarbonyl)norbornene

Product 1

HCID 867594588,9-Di(tetrahydropyranyloxycarbonyl)tetracyclo[4.4.0.12,5.17,10]dodeca-3-ene

Procedure

Of these norbornene derivativeses (β-1), 5-t-butoxycarbonylnorbornene, 5,6-di(t-butoxycarbonyl)norbornene, 5,6-di(t-butoxycarbonylmethoxycarbonyl)norbornene, 8-t-butoxycarbonyltetracyclo[4.4.0.12,5.17,10]dodeca-3-ene, 8-methyl-8-t-butoxycarbonyl)tetracyclo[4.4.0.12,5.17,10]dodeca-3-ene, 8-methyl-8-t-butoxycarbonylmethoxycarbonyl)tetracyclo[4.4.0.12,5.17,10]dodeca-3-ene, and the like are preferable.

Sources & evidence

ORD record
ord-40e44a99cc40499eb49b38c3155ba917
Source dataset
uspto-grants-2004_06
Patent number
US06753124B2

Reaction notes

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