Hydrochloric Acid → Morphinan-3,14-diol

HRID 1391282Notes

Reaction equation

HRID 1391282 reaction equation
Cl.Cl.C([O:6][C:7]1[CH:8]=[CH:9][C:10]2[CH2:11][C@H:12]3[NH:23][CH2:22][CH2:21][C@@:18]4([C:19]=2[CH:20]=1)[C@@:13]3([O:24]C(=O)C)[CH2:14][CH2:15][CH2:16][CH2:17]4)(=O)C.Cl.C([O:32][C:33]1[CH:34]=[CH:35][C:36]2[CH2:37][C@H:38]3[NH:49][CH2:48][CH2:47][C@@:44]4([C:45]=2[CH:46]=1)[C@@:39]3([O:51]C(=O)C)[CH2:40][CH2:41][C:42](=[O:50])[CH2:43]4)(=O)C>>[OH:6][C:7]1[CH:8]=[CH:9][C:10]2[CH2:11][C@H:12]3[NH:23][CH2:22][CH2:21][C@@:18]4([C:19]=2[CH:20]=1)[C@@:13]3([OH:24])[CH2:14][CH2:15][CH2:16][CH2:17]4.[OH:32][C:33]1[CH:34]=[CH:35][C:36]2[CH2:37][C@H:38]3[NH:49][CH2:48][CH2:47][C@@:44]4([C:45]=2[CH:46]=1)[C@@:39]3([OH:51])[CH2:40][CH2:41][C:42](=[O:50])[CH2:43]4

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 70605493HCID 70605493, compoundHCID 70606414HCID 70606414, compound

Product 2

HCID 5490068Morphinan-3,14-diolHCID 57466901HCID 57466901, compound

Procedure

In accordance with the above procedure, but where in place of 3,14-diacetylnoroxymorphone (4a) there is subjected to the acid hydrolysis 3,14-diacetoxymorphinan hydrochloride (4e) or 3,14-diacetoxy-6-oxomorphinan hydrochloride (4f) there are obtained the corresponding 3,14-dihydroxymorphinan (5e) and 3,14-dihydroxy-6-oxomorphinan (5f).

Sources & evidence

ORD record
ord-75902eb8eacf431ea7e427cb0702ac53
Source dataset
uspto-grants-1979_02
Patent number
US04141897

Reaction notes

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