HCID 10839444, compound → HCID 10648455, compound

HRID 430871Notes

Reaction equation

HRID 430871 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1[P:25]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=O)(=O)[CH3:2]>O1CCCC1>[CH2:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1[P:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[CH3:2]

Participants

3

Reactant 1

HCID 10839444HCID 10839444, compound2×

Product 1

HCID 10648455HCID 10648455, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

127 mg (0.25 mmol) of (−)-2-acetylamino-2′-diphenylphosphinyl-1,1′-binaphthyl (the formula (1-2a-1)) was dissolved in 6 ml of tetrahydrofuran under the flow of nitrogen. To the solution, 620 μl (1.24 mmol) of tetrahydrofuran solution (2M) of borane-dimethyl sulfide complex was added at 0° C., followed by the stirring for 18 hours at 88° C. The reaction solution was extracted with 50 ml of ethyl acetate, washed with 10 ml of saturated aqueous solution of ammonium chloride and 10 ml of brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure. To the residue, 6 ml of diethylamine was added and stirred under room temperature for 3 hours. Diethylamine was evaporated under a reduced pressure and the residue was purified using a silica gel column chromatography (eluent: 1:50 mixture of ethyl acetate and hexane) to obtain 91 mg of the titled compound.

Workup

  1. customstirring for 18 hours
  2. customat 88° C
  3. extractionThe reaction solution was extracted with 50 ml of ethyl acetate
  4. washwashed with 10 ml of saturated aqueous solution of ammonium chloride and 10 ml of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under a reduced pressure
  7. additionTo the residue, 6 ml of diethylamine was added
  8. customDiethylamine was evaporated under a reduced pressure
  9. customthe residue was purified
  10. additiona silica gel column chromatography (eluent: 1:50 mixture of ethyl acetate and hexane)

Sources & evidence

ORD record
ord-0da14cf1fb5c45d081397a372850cbed
Source dataset
uspto-grants-2001_11
Patent number
US06323353B1

Reaction notes

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