HCID 11272493, compound → HCID 12010726, compound

HRID 430866Notes

Reaction equation

HRID 430866 reaction equation
CO[C:3]([NH:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1[P:26]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=O)=O>O1CCCC1>[CH3:3][NH:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1[P:26]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

3

Reactant 1

HCID 11272493HCID 11272493, compound2×

Product 1

HCID 12010726HCID 12010726, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.59 gram (6.81 mmol) of (−)-2-methoxycarbonylamino-2′-diphenylphosphinyl-1,1′-binaphthyl (the formula (1-2b-1)) was dissolved in 170 ml of tetrahydrofuran, under the flow of nitrogen. To the solution, 27.2 ml of tetrahydrofuran solution (2M) of borane-dimethyl sulfide complex was added at 0° C. over 30 minutes and the resultant mixture was stirred for 18 hours at 88° C. The resultant reaction solution was extracted with 300 ml of ethyl acetate, and the extract was washed with 100 ml of saturated aqueous solution of ammonium chloride and 100 ml of brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure. To the residue, 272 ml of diethylamine was added and stirred at room temperature for 30 minutes. After evaporating diethylamine, the residue was purified using a silica gel column chromatography (eluent: 1:16 mixture of ethyl acetate and hexane) to obtain 3.05 gram of the titled compound.

Workup

  1. customThe resultant reaction solution
  2. extractionwas extracted with 300 ml of ethyl acetate
  3. washthe extract was washed with 100 ml of saturated aqueous solution of ammonium chloride and 100 ml of brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under a reduced pressure
  6. additionTo the residue, 272 ml of diethylamine was added
  7. customAfter evaporating diethylamine
  8. customthe residue was purified
  9. additiona silica gel column chromatography (eluent: 1:16 mixture of ethyl acetate and hexane)

Sources & evidence

ORD record
ord-e9e39431fc384e05b53c791d07cd8441
Source dataset
uspto-grants-2001_11
Patent number
US06323353B1

Reaction notes

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