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)-pyrrolidine

HRID 2055037Notes

Reaction equation

HRID 2055037 reaction equation
[C:1]([Si:5]([CH3:50])([CH3:49])[O:6][C:7]1[CH:8]=[CH:9][C:10]([C:14]2[CH2:15][O:16][C:17]3[C:22]([C:23]=2[C:24]([OH:40])([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][N:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)=[CH:28][CH:27]=2)[CH3:25])=[CH:21][CH:20]=[C:19]([O:41][Si:42]([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:44])[CH3:43])[CH:18]=3)=[C:11](O)[CH:12]=1)([CH3:4])([CH3:3])[CH3:2].Cl>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[C:45]([Si:42]([CH3:44])([CH3:43])[O:41][C:19]1[CH:20]=[CH:21][C:22]2[C:23]3[C:24]([C:26]4[CH:27]=[CH:28][C:29]([O:32][CH2:33][CH2:34][N:35]5[CH2:36][CH2:37][CH2:38][CH2:39]5)=[CH:30][CH:31]=4)([CH3:25])[O:40][C:9]4[CH:8]=[C:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:2])[CH3:3])([CH3:49])[CH3:50])[CH:12]=[CH:11][C:10]=4[C:14]=3[CH2:15][O:16][C:17]=2[CH:18]=1)([CH3:46])([CH3:48])[CH3:47]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 219591555-(Tert-butyl-dimethyl-silyloxy)-2-(7-(tert-butyl-dimethyl-silyloxy)-4-{1-hydroxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-ethyl}-2H-chromen-3-yl)phenol

Product 1

HCID 219592841-(2-{4-[2,8-Bis-(tert-butyl-dimethyl-silyloxy)-5-methyl-5,11-dihydro-chromeno[4,3-c]chromen-5-yl]-phenoxy}-ethyl)-pyrrolidine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(Tert-butyl-dimethyl-silyloxy)-2-(7-(tert-butyl-dimethyl-silyloxy)-4-{1-hydroxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-ethyl}-2H-chromen-3-yl)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. The mixture was then diluted with water and ethyl acetate. The layers were separated and the 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 to yield the title compound as a light oil.

Workup

  1. customThe layers were separated
  2. washthe organic 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-2273ac70308f4068b99ec9d8090d9033
Source dataset
uspto-grants-2008_02
Patent number
US07329654B2

Reaction notes

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