HCID 18357468, compound → HCID 9908628, compound

HRID 428056Notes

Reaction equation

HRID 428056 reaction equation
[N:1]([CH:4]([CH2:21][CH:22]=[CH2:23])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)=[N+]=[N-].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.C(OCC)C>[NH2:1][CH:4]([CH2:21][CH:22]=[CH2:23])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][N:13]=1

Participants

5

Reactant 2

HCID 18357468HCID 18357468, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 9908628HCID 9908628, compoundYield 54.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 631 mg of 3-[2-(2-azido-4-pentenyl)phenyl]-1,2-benzisoxazole in 10 ml of anhydrous tetrahydrofuran at -40° C. under a nitrogen atmosphere was added 2.07 ml of a 1 M solution of lithium aluminium hydride in diethyl ether. The reaction mixture was warmed to room temperature then heated to 60° C. for 1 h. After cooling to room temperature and careful quenching with 4 N sodium hydroxide, 50 ml of water was added and the product extracted with 100 ml then 50 ml of dichloromethane. The combined organic extracts were dried over sodium sulfate and the solvent removed by evaporation to give crude product which was purified by chromatography on silica gel eluting with 10% methanol in dichloromethane, to give 315 mg of 3-[2-(2-amino-4-pentenyl)phenyl]-1,2-benzisoxazole. The product was dissolved in 1 ml of methanol and 131 mg of fumaric acid was added. Addition of diethyl ether and cooling to 4° C. led to crystallisation of 313 mg of 3-[2-(2-amino-4-pentenyl)phenyl]-1,2-benzisoxazole (E)-butenedioate, melting at 170-172° C.

Workup

  1. temperaturethen heated to 60° C. for 1 h
  2. temperatureAfter cooling to room temperature
  3. customcareful quenching with 4 N sodium hydroxide, 50 ml of water
  4. additionwas added
  5. extractionthe product extracted with 100 ml
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. customthe solvent removed by evaporation
  8. customto give crude product which
  9. customwas purified by chromatography on silica gel eluting with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-b342d9781f2c4ca19b3e25802cce1bcf
Source dataset
uspto-grants-2001_11
Patent number
US06313139B1

Reaction notes

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