Benzyl Alcohol → HCID 76529972, compound

HRID 1454792Notes

Reaction equation

HRID 1454792 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C@@H:10]1[CH2:19][CH2:18][C:13]2([O:17][CH2:16][CH2:15][O:14]2)[CH2:12][C@H:11]1C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.C([N:42]([CH2:45]C)CC)C.[CH2:47]([OH:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH:10]1[CH2:19][CH2:18][C:13]2([O:14][CH2:15][CH2:16][O:17]2)[CH2:12][CH:11]1[NH:42][C:45](=[O:30])[O:54][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 86616051HCID 86616051, compound

Product 1

HCID 76529972HCID 76529972, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A stirred solution of trans 8-(2,4,5-trifluorophenyl)-1,4-dioxaspiro[4.5]decane-7-carboxylic acid (500 mg, 1.29 mmol) in toluene (20 mL) was treated with diphenylphosphoryl azide (0.33 mL, 1.55 mmol), triethylamine (0.22 mL, 1.55 mmol) and anhydrous benzyl alcohol (0.33 mL, 3.2 mmol) at room temperature under a nitrogen atmosphere. After heating at 90° C. for 2 days, the reaction mixture was evaporated under reduced pressure and the residue was diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate solution. The organic phase was dried over anhydrous sodium sulfate and evaporated to yield the crude product which was purified by chromatography on a Biotage® system (silica gel, ethyl acetate in hexanes gradient 25-40%) to yield the title compound.

Workup

  1. customthe reaction mixture was evaporated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with saturated aqueous sodium bicarbonate solution
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. customevaporated
  6. customto yield the crude product which
  7. customwas purified by chromatography on a Biotage® system (silica gel, ethyl acetate in hexanes gradient 25-40%)

Sources & evidence

ORD record
ord-3a194a590c114bdfaa8cef81b89e5482
Source dataset
uspto-grants-2009_01
Patent number
US07482336B2

Reaction notes

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