Benzyl Alcohol → HCID 57069049, compound

HRID 982127Notes

Reaction equation

HRID 982127 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:15]3[C@H]([CH2:10][C@H:11]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:12][C:13]=3[CH:14]=1)[C@H](C(O)=O)[CH2:7][CH2:6]2.C([N:27]([CH2:30]C)[CH2:28][CH3:29])C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:39])C=CC=CC=1.[CH2:49]([OH:56])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>C1(C)C=CC=CC=1>[C:30]([NH:27][C@H:28]1[C@H:29]2[C:15]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:14][C:13]=3[CH2:12][C@@H:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10]2)[CH2:6][CH2:7]1)([O:56][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:39]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 57185439HCID 57185439, compound

Product 1

HCID 57069049HCID 57069049, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

[1R,8S,9aR] 5-Methoxy-8-phenyl-2,3,7,8,9,9a-hexahydrophenalene-1-carboxylic acid (0.74 g, 2.3 mmol), from Step 5, and triethylamine (0.32 mL, 2.3 mmol) are dissolved in 16 mL of toluene and 0.55 mL (2.5 mmol) of diphenylphosphoryl azide is added. The mixture is heated at 80° C. for 2.5 hours then 0.5 mL (4.8 mmol) of benzyl alcohol is added and heating is continued at 80° C. for an additional 3 hours and at 65° C. for 15 hours. The mixture is cooled and concentrated under reduced pressure and 25 mL of diethyl ether is added. The solution is washed with 10 mL of 1N aqueous sodium hydroxide solution and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The product is purified by chromatography on silica gel to give the title compound.

Workup

  1. temperatureheating
  2. temperatureThe mixture is cooled
  3. concentrationconcentrated under reduced pressure and 25 mL of diethyl ether
  4. additionis added
  5. washThe solution is washed with 10 mL of 1N aqueous sodium hydroxide solution and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe product is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-b2df16c9d6da4e169c3b5b89b099469c
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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