HCID 70220605, compound → HCID 54257512, compound

HRID 567435Notes

Reaction equation

HRID 567435 reaction equation
Cl.Cl.[CH:3]1([CH2:6][N:7]2[CH2:25][CH2:24][C@:14]34[C:15]5[C:16]6[O:23][C@H:13]3[C@H:12]([N:26](CC3C=CC=CC=3)[CH:27]([CH3:29])[CH3:28])[CH2:11][CH2:10][C@@:9]4([OH:37])[C@H:8]2[CH2:21][C:20]=5[CH:19]=[CH:18][C:17]=6[OH:22])[CH2:5][CH2:4]1.Cl.Cl.[CH:40]1([CH2:43][N:44]2[CH2:62][CH2:61][C@:51]34[C:52]5[C:53]6[O:60][C@H:50]3[C@H:49]([N:63](CC3C=CC=CC=3)[CH2:64][CH:65]([CH3:67])[CH3:66])[CH2:48][CH2:47][C@@:46]4([OH:75])[C@H:45]2[CH2:58][C:57]=5[CH:56]=[CH:55][C:54]=6[OH:59])[CH2:42][CH2:41]1.Cl.Cl.[CH:78]1([CH2:81][N:82]2[CH2:100][CH2:99][C@:89]34[C:90]5[C:91]6[O:98][C@H:88]3[C@H:87]([N:101](CC3C=CC=CC=3)[CH2:102][CH2:103][CH2:104][CH3:105])[CH2:86][CH2:85][C@@:84]4([OH:113])[C@H:83]2[CH2:96][C:95]=5[CH:94]=[CH:93][C:92]=6[OH:97])[CH2:80][CH2:79]1.Cl.Cl.[CH:116]1([CH2:119][N:120]2[CH2:138][CH2:137][C@:127]34[C:128]5[C:129]6[O:136][C@H:126]3[C@H:125]([N:139](CC3C=CC=CC=3)[CH2:140][CH2:141][CH2:142][CH2:143][CH3:144])[CH2:124][CH2:123][C@@:122]4([OH:152])[C@H:121]2[CH2:134][C:133]=5[CH:132]=[CH:131][C:130]=6[OH:135])[CH2:118][CH2:117]1>>[CH:3]1([CH2:6][N:7]2[CH2:25][CH2:24][C@:14]34[C:15]5[C:16]6[O:23][C@H:13]3[C@H:12]([NH:26][CH:27]([CH3:28])[CH3:29])[CH2:11][CH2:10][C@@:9]4([OH:37])[C@H:8]2[CH2:21][C:20]=5[CH:19]=[CH:18][C:17]=6[OH:22])[CH2:4][CH2:5]1.[CH:40]1([CH2:43][N:44]2[CH2:62][CH2:61][C@:51]34[C:52]5[C:53]6[O:60][C@H:50]3[C@H:49]([NH:63][CH2:64][CH:65]([CH3:66])[CH3:67])[CH2:48][CH2:47][C@@:46]4([OH:75])[C@H:45]2[CH2:58][C:57]=5[CH:56]=[CH:55][C:54]=6[OH:59])[CH2:41][CH2:42]1.[CH:78]1([CH2:81][N:82]2[CH2:100][CH2:99][C@:89]34[C:90]5[C:91]6[O:98][C@H:88]3[C@H:87]([NH:101][CH2:102][CH2:103][CH2:104][CH3:105])[CH2:86][CH2:85][C@@:84]4([OH:113])[C@H:83]2[CH2:96][C:95]=5[CH:94]=[CH:93][C:92]=6[OH:97])[CH2:79][CH2:80]1.[CH:116]1([CH2:119][N:120]2[CH2:138][CH2:137][C@:127]34[C:128]5[C:129]6[O:136][C@H:126]3[C@H:125]([NH:139][CH2:140][CH2:141][CH2:142][CH2:143][CH3:144])[CH2:124][CH2:123][C@@:122]4([OH:152])[C@H:121]2[CH2:134][C:133]=5[CH:132]=[CH:131][C:130]=6[OH:135])[CH2:117][CH2:118]1

Participants

8

Reactant 4

HCID 70220605HCID 70220605, compoundHCID 70221359HCID 70221359, compoundHCID 86756292HCID 86756292, compoundHCID 86756294HCID 86756294, compound

Product 4

HCID 54257512HCID 54257512, compoundYield 100%HCID 70217343HCID 70217343, compoundYield 100%HCID 70219721HCID 70219721, compoundYield 100%HCID 70220200HCID 70220200, compoundYield 100%

Procedure

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%).

Sources & evidence

ORD record
ord-ae54fea57e95419bb4bc04391945d01d
Source dataset
uspto-grants-2001_01
Patent number
US06177438B1

Reaction notes

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