HCID 69428865, compound → HCID 18436353, compound

HRID 351444Notes

Reaction equation

HRID 351444 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH:20]([CH2:21][CH3:22])[CH:19]([CH3:23])[CH:18]([CH2:24][O:25][Si](C)(C)C)[CH2:17][C:16]2([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][N:40]3[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]3)=[CH:33][CH:32]=2)O)=[CH:11][CH:10]=1)C1C=CC=CC=1>C(Cl)Cl.C(OCC)(=O)C.Cl[Ti](Cl)(Cl)Cl>[CH2:21]([CH:20]1[C:15]([C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)=[C:16]([C:31]2[CH:32]=[CH:33][C:34]([O:37][CH2:38][CH2:39][N:40]3[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]3)=[CH:35][CH:36]=2)[CH2:17][CH:18]([CH2:24][OH:25])[CH:19]1[CH3:23])[CH3:22]

Participants

5

Reactant 1

HCID 69428865HCID 69428865, compound

Product 1

HCID 18436353HCID 18436353, compound

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(4-benzyloxy-phenyl)-3-ethyl-4-methyl-1-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5-trimethylsilanyloxy methyl-cyclohexanol in DCM (1 mL) was added TiCl4 (0.033 mL, 3 eq.) and the mixture stirred until reaction was done. The reaction mixture was diluted with ethyl acetate (10 mL), and washed with 5% NaHCO3 aqueous solution, then brine. The crude products was purified on HPLC to yield 4-{6-ethyl-4-hydroxymethyl-5-methyl-2-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-cyclohex-1-enyl}-phenol.

Workup

  1. washwashed with 5% NaHCO3 aqueous solution
  2. customThe crude products was purified on HPLC

Sources & evidence

ORD record
ord-48711c628bc14018a2ccdf99ef03828e
Source dataset
uspto-grants-2007_02
Patent number
US07183445B2

Reaction notes

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