Hydrochloric Acid → HCID 59199452, compound

HRID 2089510Notes

Reaction equation

HRID 2089510 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[N:12]([CH:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[C:14]2([CH3:24])[CH3:23])[CH:11]=[N:10][CH:9]=1)(C)(C)C.Cl.O1CCOCC1>>[OH:6][CH2:7][C:8]1[N:12]([CH:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[C:14]2([CH3:24])[CH3:23])[CH:11]=[N:10][CH:9]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131730557HCID 131730557, compound

Product 1

HCID 59199452HCID 59199452, compound

Procedure

To 3-[5-(tert-butyl-dimethyl-silanyloxymethyl)-imidazol-1-yl]-2,2-dimethyl-indan-1-one (370 mg, 1 mmol) is added 4N HCl in 1,4-dioxane (20 mL, 0.80 mmol). The reaction is permitted to stir for 2 hours, at which time it is quenched with saturated aqueous NaHCO3 and diluted with ethyl acetate. The layers are separated and the aqueous layer is extracted twice with ethyl acetate. The combined organic layers are dried with Na2SO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (methanol-dichloromethane, 0:1 to 1:20) to furnish 3-(5-Hydroxymethyl-imidazol-1-yl)-2,2-dimethyl-indan-1-one; HRMS: (ESI) m/z 257.1295 [(M+H)+: Calcd for C15H17N2O2: 257.1290]; 1H NMR (400 MHz, CDCl3) δ ppm 0.87 (s, 3 H), 1.46 (s, 3 H), 4.69-4.97 (m, 2 H), 5.93 (s, 1 H), 7.16 (s, 1 H), 7.19 (s, 1 H), 7.54 (d, J=7.6 Hz, 1 H), 7.65 (t, J=7.5 Hz, 1 H), 7.72-7.82 (m, 1 H), 7.93 (d, J=7.6 Hz, 1 H).

Workup

  1. customis quenched with saturated aqueous NaHCO3
  2. additiondiluted with ethyl acetate
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted twice with ethyl acetate
  5. dry with materialThe combined organic layers are dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue is purified by silica gel flash chromatography (methanol-dichloromethane, 0:1 to 1:20)

Sources & evidence

ORD record
ord-05e0a40f59a1497b8b47762fec750aed
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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