반응 #654617

ord-ae54fea57e95419bb4bc04391945d01d

반응 방정식

CC(C)N(Cc1ccccc1)[C@@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5.Cl.Cl
17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-(N-isopropylbenzylamino)morphinan dihydrochloride
CCCCN(Cc1ccccc1)[C@@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5.Cl.Cl
17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-(N-butylbenzylamino)morphinan dihydrochloride
CCCCCN(Cc1ccccc1)[C@@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5.Cl.Cl
17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-(N-pentylbenzylamino)morphinan dihydrochloride
CC(C)CN(Cc1ccccc1)[C@@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5.Cl.Cl
17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-(N-isobutylbenzylamino)morphinan dihydrochloride
→
CCCCCN[C@@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5
17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-pentylaminomorphinan
수율 100.0%
CC(C)N[C@@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5
17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-isopropylaminomorphinan
수율 100.0%
CC(C)CN[C@@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5
17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-isobutylaminomorphinan
수율 100.0%
CCCCN[C@@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5
17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-butylaminomorphinan
수율 100.0%

반응물

CC(C)N(Cc1ccccc1)[C@@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5.Cl.Cl
17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-(N-isopropylbenzylamino)morphinan dihydrochloride
CCCCN(Cc1ccccc1)[C@@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5.Cl.Cl
17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-(N-butylbenzylamino)morphinan dihydrochloride
CCCCCN(Cc1ccccc1)[C@@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5.Cl.Cl
17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-(N-pentylbenzylamino)morphinan dihydrochloride
—
6β-(N-benzyl)methylamino-17-cyclopropylmethyl-4,5α-epoxy-3,14β-dihydroxymorphinan
CC(C)CN(Cc1ccccc1)[C@@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5.Cl.Cl
17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-(N-isobutylbenzylamino)morphinan dihydrochloride

시약

없음

반응 조건

상세 조건
See reaction.notes.procedure_details.

실험 절차

The procedure of Example 6 was repeated, except that 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-(N-isopropylbenzylamino)morphinan dihydrochloride 191, 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-(N-isobutylbenzylamino)morphinan dihydrochloride 192, 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-(N-butylbenzylamino)morphinan dihydrochloride 193 and 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-(N-pentylbenzylamino)morphinan dihydrochloride 194 were used as the starting compound instead of 6β-(N-benzyl)methylamino-17-cyclopropylmethyl-4,5α-epoxy-3,14β-dihydroxymorphinan 8 hydrochloride, thereby preparing 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-isopropylaminomorphinan 195 (yield: 100%), 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-isobutylaminomorphinan 196 (yield: 100%), 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-butylaminomorphinan 197 (yield: 100%) and 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-pentylaminomorphinan 198 (yield: 100%).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US06177438B1uspto-grants-2001_01