Sodium hydride → 3-(Benzhydrylideneamino)-8-oxabicyclo[3.2.1]octane-3-carboxylic acid benzyl ester

HRID 1596016Notes

Reaction equation

HRID 1596016 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11](=[O:27])[CH2:12][N:13]=[C:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.S(C1C=CC(C)=CC=1)(O)(=O)=O.S(C1C=CC(C)=CC=1)(O)(=O)=O.O[CH2:51][C@H:52]1[CH2:56][CH2:55][C@@H:54]([CH2:57]O)[O:53]1>CN(C)C=O>[CH2:3]([O:10][C:11]([C:12]1([N:13]=[C:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:57][CH:54]2[O:53][CH:52]([CH2:56][CH2:55]2)[CH2:51]1)=[O:27])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11782449Diphenylmethylene-Glycine benzyl esterHCID 86755706cis-2,5-Bis(hydroxymethyl)tetrahydrofuran ditosylate

Product 1

HCID 540516143-(Benzhydrylideneamino)-8-oxabicyclo[3.2.1]octane-3-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of sodium hydride (0.41 grams, 17.1 mmole) in N,N-dimethylformamide (50 mL) at 0° C. is added dropwise a solution of N-diphenylmethylene glycine benzyl ester (7.8 mmole) in N,N-dimethylformamide (50 mL). After stirring for 30 minutes at room temperature, a solution of cis-2,5-bis(hydroxymethyl)-tetrahydrofuran ditosylate (4.1 grams, 9.3 mmole,)(prepared by literature methods such as those described in JOC, 47, 2429-2435 (1982)) in N,N-dimethylformamide (50 mL) is added dropwise. The reaction mixture is gradually heated to 100° C. in an oil bath and stirred at this temperature overnight. The solvent is evaporated under vacuum and the residue is taken up in water and extracted twice with diethyl ether. The combined organic extracts are washed with brine, dried over magnesium sulfate and concentrated to a crude product.

Workup

  1. additionis added dropwise
  2. temperatureThe reaction mixture is gradually heated to 100° C. in an oil bath
  3. stirringstirred at this temperature overnight
  4. customThe solvent is evaporated under vacuum
  5. extractionextracted twice with diethyl ether
  6. washThe combined organic extracts are washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated to a crude product

Sources & evidence

ORD record
ord-f130ea1fde11400c8c1d601f7c0327d6
Source dataset
uspto-grants-2001_09
Patent number
US06288246B1

Reaction notes

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