Hydrochloric Acid → HCID 69685789, compound

HRID 2088130Notes

Reaction equation

HRID 2088130 reaction equation
C([Si](C)(C)[O:6][C@H:7]1[CH2:13][CH2:12][C@H:11]2[N:14]([CH2:15][CH:16]=[CH2:17])[C@:8]1([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:9][CH2:10]2)(C)(C)C.Cl>CO>[C:18]1([C@@:8]23[N:14]([CH2:15][CH:16]=[CH2:17])[C@@H:11]([CH2:10][CH2:9]2)[CH2:12][CH2:13][C@@H:7]3[OH:6])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20722845HCID 20722845, compound

Product 1

HCID 69685789HCID 69685789, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (1S,2S,5S)-2-(tertbutyldimethylsilyloxy)-1-phenyl-8-(prop-2-enyl)-8-azabicyclo[3.2.1]octane (Description 56; 230 mg, 0.64 mmol), 2M hydrochloric acid (3 ml) and methanol (6 ml) was stirred at +55° C. over 5 days, then concentrated in vacuo and quenched with saturated aqueous NaHCO3. The mixture was extracted with dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (dichloromethane:methanol:ammonia) to give the title compound (116 mg, 74%).

Workup

  1. concentrationconcentrated in vacuo
  2. customquenched with saturated aqueous NaHCO3
  3. extractionThe mixture was extracted with dichloromethane
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel (dichloromethane:methanol:ammonia)

Sources & evidence

ORD record
ord-9ec62808a9064a3fa95b80cb1333e471
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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