Hydrochloric Acid → (1RS,2RS,4SR)-3-(2-dimethylaminomethyl-1-hydroxy-4-phenethyl-cyclohexyl)-phenol hydrochloride

HRID 2392760Notes

Reaction equation

C([O:8][C:9]1[CH:10]=[C:11]([C:15]2([OH:33])[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:17][CH:16]2[CH2:29][N:30]([CH3:32])[CH3:31])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.Cl.C[Si](C)(C)[Cl:37].O>>[ClH:37].[CH3:31][N:30]([CH2:29][CH:16]1[CH2:17][CH:18]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:19][CH2:20][C:15]1([C:11]1[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][CH:12]=1)[OH:33])[CH3:32]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 189805081-(3-Benzyloxyphenyl)-2-dimethylaminomethyl-4-phenethyl-cyclohexanol

HCID 86753056Chlorotrimethylsilane water

Product 1

HCID 18980488(1RS,2RS,4SR)-3-(2-dimethylaminomethyl-1-hydroxy-4-phenethyl-cyclohexyl)-phenol hydrochlorideYield 63%

Procedure

Compound (50) was hydrogenated corresponding to the conditions described in Example 23, step 2. The base obtained was converted into the hydrochloride with trimethylchlorosilane/water. Compound (49) was obtained in a yield of 63% theoretical.

Workup

customThe base obtained

Sources & evidence

ORD record: ord-972526bbaa5a4c5ea939fe2b93a50068
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05801201

Reaction notes

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