Hydrochloric Acid → HCID 67548083, compound

HRID 2089550Notes

Reaction equation

HRID 2089550 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[N:12]([CH:13]2[C:21]3[C:16](=[C:17]([Cl:22])[CH:18]=[CH:19][CH:20]=3)[C:15](=[O:23])[C:14]2([CH3:25])[CH3:24])[CH:11]=[N:10][CH:9]=1)(C)(C)C.Cl.C(OCC)C>CO.C([O-])(O)=O.[Na+]>[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:16]=1[C:15](=[O:23])[C:14]([CH3:25])([CH3:24])[CH:13]2[N:12]1[C:8]([CH2:7][OH:6])=[CH:9][N:10]=[CH:11]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 131730560HCID 131730560, compound

Product 1

HCID 67548083HCID 67548083, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-[5-(tert-butyl-dimethyl-silanyloxymethyl)-imidazol-1-yl]-7-chloro-2,2-dimethyl-indan-1-one (650 mg, 1.6 mmol) in methanol (20 mL) is added a 1N solution of HCl in diethyl ether (15 mL, 15 mmol). The reaction is permitted to stir for 30 minutes, at which time the reaction is cooled to 0° C. and diluted with saturated aqueous NaHCO3. The reaction mixture is then concentrated in vacuo to ca. one fourth of the original volume and diluted with ethyl acetate. The layers are separated and the aqueous layer is extracted two times with ethyl acetate. The combined organic extracts are dried over Na2SO4, filtered and concentrated. The resulting residue is purified by silica gel flash chromatography (methanol-dichloromethane, 0:1 to 1:19) to furnish 7-chloro-3-(5-hydroxymethyl-imidazol-1-yl)-2,2-dimethyl-indan-1-one; 1H NMR (400 MHz, CD3OD) δ ppm 0.86 (s, 3 H), 1.41 (s, 3 H), 4.77 (dd, 2 H); 5.88 (s, 1 H), 7.01 (s, 1 H), 7.09 (s, 1 H), 7.45 (d, J=7.58 Hz, 1 H), 7.62 (d, J=7.83 Hz, 1 H), 7.74 (t, J=7.71 Hz, 1 H); HRMS: (ESI) m/z 291.0898 [(M+H)+: Calcd for C15H16N2O2Cl: 291.0900].

Workup

  1. concentrationThe reaction mixture is then concentrated in vacuo to ca. one fourth of the original volume
  2. additiondiluted with ethyl acetate
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted two times with ethyl acetate
  5. dry with materialThe combined organic extracts are dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue is purified by silica gel flash chromatography (methanol-dichloromethane, 0:1 to 1:19)

Sources & evidence

ORD record
ord-dfe7eb8c3066432d9bf252661d66d77f
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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