Hydrochloric Acid → 1-(2-{4-[2,8-Bis-(tert-butyl-dimethyl-silyloxy)-5-methyl-5,11-dihydro-chromeno[4,3-c]chromen-5-yl]-phenoxy}-ethyl)-azepane

HRID 2214298Notes

Reaction equation

HRID 2214298 reaction equation
[N:1]1([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])=[CH:27][CH:28]=4)[O:23][CH2:22][C:21]=3[C:38]3[CH:43]=[CH:42][C:41]([O:44][Si:45]([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:47])[CH3:46])=[CH:40][C:39]=3O)([OH:19])[CH3:18])=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[C:34]([Si:31]([CH3:32])([CH3:33])[O:30][C:26]1[CH:27]=[CH:28][C:29]2[C:20]3[C:17]([C:14]4[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH2:8][N:1]5[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]5)=[CH:12][CH:13]=4)([CH3:18])[O:19][C:39]4[CH:40]=[C:41]([O:44][Si:45]([C:48]([CH3:50])([CH3:51])[CH3:49])([CH3:47])[CH3:46])[CH:42]=[CH:43][C:38]=4[C:21]=3[CH2:22][O:23][C:24]=2[CH:25]=1)([CH3:35])([CH3:36])[CH3:37]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 693277712-[4-{-1-[4-(2-azepan-1-yl-ethoxy)-phenyl]-1-hydroxy-ethyl}-7-(tert-butyl-dimehyl-silyloxy)-2H-chromen-3-yl]-5-(tert-butyl-dimethyl-silyloxy)-phenol

Product 1

HCID 219592481-(2-{4-[2,8-Bis-(tert-butyl-dimethyl-silyloxy)-5-methyl-5,11-dihydro-chromeno[4,3-c]chromen-5-yl]-phenoxy}-ethyl)-azepane

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-[4-{1-[4-(2-azepan-1-yl-ethoxy)-phenyl]-1-hydroxy-ethyl}-7-(tert-butyl-dimehyl-silyloxy)-2H-chromen-3-yl]-5-(tert-butyl-dimethyl-silyloxy)-phenol, prepared as in STEP A above, was dissolved in toluene (8 mL) and treated with diluted HCl (0.4 mL of concentrated HCl:H2O=1:2 v/v). The reaction mixture was vigorously stirred at room temperature for 1.5 h, then diluted with water and ethyl acetate. The resulting layers were separated and organic layer washed successively with saturated NaHCO3, brine and dried over MgSO4. The desiccant was filtered off, and the filtrate concentrated. Flash chromatography with ethyl acetate:hexane:CH3OH (containing 1% NH4OH)=49:49:2 as the eluent yielded the title compound as a light yellow oil.

Workup

  1. customThe resulting layers were separated
  2. washorganic layer washed successively with saturated NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. filtrationThe desiccant was filtered off
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-82f97b7d123945038df2a330bf61f707
Source dataset
uspto-grants-2006_09
Patent number
US07105679B2

Reaction notes

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