1,2-Dibromoethane → (1RS,2RS,4SR)-2-dimethylaminomethyl-4-isobutoxy-(3-methylsulphanyl-phenyl)-cyclohexanol hydrochloride

HRID 2392745Notes

Reaction equation

HRID 2392745 reaction equation
Cl.[CH3:2][N:3]([CH2:5][CH:6]1[CH2:11][CH:10]([O:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:9][CH2:8][C:7]1=[O:17])[CH3:4].Br[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([S:25][CH3:26])[CH:20]=1.BrCCBr.C[Si](C)(C)[Cl:33].O>CCOCC>[ClH:33].[CH3:4][N:3]([CH2:5][CH:6]1[CH2:11][CH:10]([O:12][CH2:13][CH:14]([CH3:15])[CH3:16])[CH2:9][CH2:8][C:7]1([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([S:25][CH3:26])[CH:20]=1)[OH:17])[CH3:2]

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 27356273-BromothioanisoleHCID 189805002-Dimethylaminomethyl-4-isobutoxy-cyclohexanone hydrochlorideHCID 86753056Chlorotrimethylsilane water

Product 1

HCID 18980483(1RS,2RS,4SR)-2-dimethylaminomethyl-4-isobutoxy-(3-methylsulphanyl-phenyl)-cyclohexanol hydrochlorideYield 32%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Compound (22) was reacted with 1-bromo-3-methylsulphanyl-benzene corresponding to the conditions described in Example 1. In departure from the conditions described in Example 1, ether was used as the solvent and 1,2-dibromoethane was added to the batch in order to increase the yield. The crude product obtained was purified with diisopropyl ether via a silica gel column, and was taken up in tetrahydrofuran/ether. The crystals obtained after adding trimethylchlorosilane/water were recrystallised from ethyl acetate. Compound (23) was obtained in a yield of 32% theoretical.

Workup

  1. additionwas added to the batch in order
  2. temperatureto increase the yield
  3. customThe crude product obtained
  4. customwas purified with diisopropyl ether via a silica gel column
  5. customThe crystals obtained
  6. customwere recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-677f11368ebe4dfa8730a75190011983
Source dataset
uspto-grants-1998_09
Patent number
US05801201

Reaction notes

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