(5a,6a)-17-(Cyclopropylmethyl)-4,5-epoxy-6-(methylamino)-morphinan-3,14-diol → 17-cyclopropylmethyl-4,5alpha-epoxy-3,14beta-dihydroxy-7beta-(N-methyl-3-trifluoromethoxycinnamamido)morphinan hydrochloride

HRID 567437Notes

Reaction equation

HRID 567437 reaction equation
[CH:1]1([CH2:4][N:5]2[CH2:23][CH2:22][C@:12]34[C:13]5[C:14]6[O:21][C@H:11]3[CH2:10][C@@H:9]([NH:24][CH3:25])[CH2:8][C@@:7]4([OH:26])[C@H:6]2[CH2:19][C:18]=5[CH:17]=[CH:16][C:15]=6[OH:20])[CH2:3][CH2:2]1.[CH:27]1([CH2:30][N:31]2[CH2:49][CH2:48][C@:38]34[C:39]5[C:40]6[O:47][C@H:37]3[CH2:36][C@H:35]([NH:50][CH3:51])[CH2:34][C@@:33]4([OH:52])[C@H:32]2[CH2:45][C:44]=5[CH:43]=[CH:42][C:41]=6[OH:46])[CH2:29][CH2:28]1.C1(CN2CC[C@]34C5C6O[C@H]3[C@@H](NC)CC[C@@]4(O)[C@H]2CC=5C=CC=6O)CC1.[F:79][C:80]([F:94])([F:93])[O:81][C:82]1[CH:83]=[C:84]([CH:90]=[CH:91][CH:92]=1)[CH:85]=[CH:86][C:87]([Cl:89])=[O:88]>>[ClH:89].[CH:1]1([CH2:4][N:5]2[CH2:23][CH2:22][C@:12]34[C:13]5[C:14]6[O:21][C@H:11]3[CH2:10][C@@H:9]([N:24]([CH3:25])[C:87](=[O:88])[CH:86]=[CH:85][C:84]3[CH:90]=[CH:91][CH:92]=[C:82]([O:81][C:80]([F:94])([F:93])[F:79])[CH:83]=3)[CH2:8][C@@:7]4([OH:26])[C@H:6]2[CH2:19][C:18]=5[CH:17]=[CH:16][C:15]=6[OH:20])[CH2:2][CH2:3]1.[ClH:89].[CH:27]1([CH2:30][N:31]2[CH2:49][CH2:48][C@:38]34[C:39]5[C:40]6[O:47][C@H:37]3[CH2:36][C@H:35]([N:50]([CH3:51])[C:87](=[O:88])[CH:86]=[CH:85][C:84]3[CH:90]=[CH:91][CH:92]=[C:82]([O:81][C:80]([F:94])([F:93])[F:79])[CH:83]=3)[CH2:34][C@@:33]4([OH:52])[C@H:32]2[CH2:45][C:44]=5[CH:43]=[CH:42][C:41]=6[OH:46])[CH2:28][CH2:29]1

Participants

6

Reactant 4

HCID 15908858(5a,6a)-17-(Cyclopropylmethyl)-4,5-epoxy-6-(methylamino)-morphinan-3,14-diolHCID 538952143-Trifluoromethoxycinnamoyl chlorideHCID 7022076817-Cyclopropylmethyl-4,5alpha-epoxy-3,14beta-dihydroxy-7beta-methylaminomorphinanHCID 7022155017-Cyclopropylmethyl-4,5alpha-epoxy-3,14beta-dihydroxy-7alpha-methylaminomorphinan

Product 2

HCID 8675629817-cyclopropylmethyl-4,5alpha-epoxy-3,14beta-dihydroxy-7alpha-(N-methyl-3-trifluoromethoxycinnamamido)morphinan hydrochlorideYield 68%HCID 8675630017-cyclopropylmethyl-4,5alpha-epoxy-3,14beta-dihydroxy-7beta-(N-methyl-3-trifluoromethoxycinnamamido)morphinan hydrochlorideYield 71%

Procedure

The procedure of Example 11 was repeated, except that 17-cyclopropylmethyl-4,5α-epoxy-3,14β-dihydroxy-7α-methylaminomorphinan and 17-cyclopropylmethyl-4,5α-epoxy-3,14β-dihydroxy-7β-methylaminomorphinan were used instead of 17-cyclopropylmethyl-4,5α-epoxy-3,14β-dihydroxy-6α-methylaminomorphinan 4 and 3-trifluoromethoxycinnamoyl chloride was used instead of 3,4-dichlorophenylacetyl chloride, thereby preparing 17-cyclopropylmethyl-4,5α-epoxy-3,14β-dihydroxy-7α-(N-methyl-3-trifluoromethoxycinnamamido)morphinan hydrochloride 243 (yield: 68%) and 17-cyclopropylmethyl-4,5α-epoxy-3,14β-dihydroxy-7β-(N-methyl-3-trifluoromethoxycinnamamido)morphinan hydrochloride 244 (yield: 71%).

Sources & evidence

ORD record
ord-5275fd381aab44369151df181e0a223d
Source dataset
uspto-grants-2001_01
Patent number
US06177438B1

Reaction notes

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