Ammonia → HCID 68430664, compound

HRID 2092018Notes

Reaction equation

HRID 2092018 reaction equation
[CH3:1][O:2][CH2:3][O:4][CH2:5][C:6]1[CH:7]2[CH2:12][CH:9]([CH2:10][CH:11]=1)[C:8]2([CH3:14])[CH3:13].B.[O:16]1CCCC1.N.Cl[O-].[Na+].Cl>O1CCCC1>[CH3:1][O:2][CH2:3][O:4][CH2:5][CH:6]1[CH:11]([OH:16])[CH2:10][CH:9]2[CH2:12][CH:7]1[C:8]2([CH3:14])[CH3:13]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 13114595HCID 13114595, compoundHCID 23665760Sodium Hypochlorite

Product 1

HCID 68430664HCID 68430664, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To rac-2-[(methoxymethoxy)methyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene (3.00 g, 15.3 mmol) in tetrahydrofuran (25 mL), a borane-tetrahydrofuran complex (0.99 M in tetrahydrofuran, 12 mL) was added gradually dropwise at 0° C., and then the resulting reaction solution was warmed to room temperature and stirred for 1 days. The reaction solution was cooled to 0° C., and 28 mass % aqueous ammonia (2 mL) and about 8 mass % aqueous sodium hypochlorite (28 g) were added gradually dropwise successively. The reaction solution was warmed to room temperature and stirred for 1 day. After completion of the reaction, the reaction solution was mixed with 1 M aqueous hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate=10/1→4/1) to give rac-2-[(methoxymethoxy)methyl]-6,6-dimethylbicyclo[3.1.1]heptan-3-ol.

Workup

  1. customthe resulting reaction solution
  2. temperatureThe reaction solution was cooled to 0° C.
  3. temperatureThe reaction solution was warmed to room temperature
  4. stirringstirred for 1 day
  5. customAfter completion of the reaction
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. customevaporated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate=10/1→4/1)

Sources & evidence

ORD record
ord-93a02c4f41ac4664b79bf0ebfa69ac76
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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