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

HRID 2185616Notes

Reaction equation

HRID 2185616 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)C=C2.[C:8]([O:12][C:13]([CH:15]1[CH2:20][CH:19]2[CH2:21][CH:16]1[CH:17]=[CH:18]2)=[O:14])([CH3:11])(C)C.C(OC(C1[CH:34]([C:35]([O:37][C:38](C)(C)C)=[O:36])[CH:33]2[CH2:42][CH:30]1C=C2)=O)(C)(C)C.C(OC(C[O:51][C:52]([CH:54]1C(C(OCC(OC(C)(C)C)=O)=O)C2C[CH:55]1C=C2)=O)=O)(C)(C)C.C([O:76]C1C(=C=O)C2CC1C1C2C2CC1C=C2)(C)(C)C.CC1(C(OC(C)(C)C)=O)CC2CC1C1C2C2CC1C=C2.CC1(C(OCC(OC(C)(C)C)=O)=O)CC2CC1C1C2C2CC1C=C2>>[O:36]1[CH2:30][CH2:42][CH2:33][CH2:34][CH:35]1[O:37][C:38]([CH:20]1[CH:15]([C:13]([O:12][CH:8]2[CH2:11][CH2:55][CH2:54][CH2:52][O:51]2)=[O:14])[CH:16]2[CH2:21][CH:19]1[CH:18]1[CH:17]2[CH:6]2[CH2:5][CH:4]1[CH:7]=[CH:1]2)=[O:76]

Participants

8

Reactant 7

HCID 103522-NorborneneHCID 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)norborneneHCID 233771928-Methyl-8-t-butoxycarbonylmethoxycarbonyltetracyclo[4.4.0.12.5.17.10]dodec-3-eneHCID 69265029Tert-butyl 4-methyltetracyclo[6.2.1.13,6,02,7]dodec-9-ene-4-carboxylateHCID 1317232598-t-Butoxy-carbonyltetracyclo[4.4.0.12.5.17.10]dodec-3-ene

Product 1

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

Procedure

Among these norbornene derivatives (3), 5-t-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-di(t-butoxy-carbonyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(t-butoxycarbonyl-methoxycarbonyl)bicyclo[2.2.1]hept-2-ene, 8-t-butoxy-carbonyltetracyclo[4.4.0.12.5.17.10]dodec-3-ene, 8-methyl-8-t-butoxycarbonyltetracyclo[4.4.0.12.5.17.10]dodec-3-ene, 8-methyl-8-t-butoxycarbonylmethoxycarbonyltetracyclo[4.4.0.12.5.17.10]dodec-3-ene are preferred.

Sources & evidence

ORD record
ord-5b75a015600d45799b0b64004968b02b
Source dataset
uspto-grants-2002_06
Patent number
US06403280B1

Reaction notes

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