Benzyl Alcohol → HCID 58192798, compound

HRID 38452Notes

Reaction equation

HRID 38452 reaction equation
[O:1]=[C:2]1[CH:9]2[CH2:10][C:5]3(C(O)=O)[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.C([N:17]([CH2:20]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.[CH2:39]([OH:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:39]([O:46][C:20](=[O:29])[NH:17][C:5]12[CH2:4][CH:3]3[CH2:11][CH:7]([CH2:8][CH:9]([C:2]3=[O:1])[CH2:10]1)[CH2:6]2)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 28425154-Oxoadamantane-1-carboxylic acid

Product 1

HCID 58192798HCID 58192798, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

0.7 g of 4-Oxo-adamantane-1-carboxylic acid (11) were codistilled twice with toluene and dissolved in 5.5 mL of dry toluene. 1.1 mL of triethylamine were added. At 0° C., 0.9 mL of diphenylphosphoryl azide were added dropwise. The mixture was allowed to warm to room temperature and then the mixture was put into a preheated bath at 90° C. The mixture was heated until gas evolution ceased (ca. 1.5 h). 1.9 mL of benzyl alcohol were added and stirring was continued at 100° C. When the reaction was complete, it was cooled to room temperature, then ethyl acetate was added and the mixture was extracted twice with 1M aqueous sodium carbonate solution. The aqueous layer was extracted with ethyl acetate and the combined organic layer was dried over sodium sulphate and evaporated. The resulting oil was subjected to silica gel chromatography (heptanes:ethyl acetate) to give 871 mg of the desired product. Rt=1.40 min (Method 3). Detected mass: 300.2 (M+H+).

Workup

  1. customthe mixture was put into a preheated bath at 90° C
  2. temperatureThe mixture was heated until gas evolution
  3. custom(ca. 1.5 h)
  4. customwas continued at 100° C
  5. temperatureit was cooled to room temperature
  6. extractionthe mixture was extracted twice with 1M aqueous sodium carbonate solution
  7. extractionThe aqueous layer was extracted with ethyl acetate
  8. dry with materialthe combined organic layer was dried over sodium sulphate
  9. customevaporated

Sources & evidence

ORD record
ord-5ce4ea56a24644e28963542948ca5db0
Source dataset
uspto-grants-2013_09
Patent number
US08524737B2

Reaction notes

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