HCID 12010730, compound → HCID 12010731, compound

HRID 430872Notes

Reaction equation

HRID 430872 reaction equation
[C:1]([NH:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1[P:30]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1>[CH2:1]([NH:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1[P:30]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 12010730HCID 12010730, compound2×

Product 1

HCID 12010731HCID 12010731, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

29 mg (0.05 mmol) of (−)-2-benzoylamino-2′-diphenylphosphinyl-1,1′-binaphthyl (the formula (1-2c-1)) was dissolved in 1.3 ml of tetrahydrofuran under the flow of nitrogen. To the solution, 88 μl (0.18 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. The extract was washed with 10 ml of saturated 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, 1.5 ml of diethylamine was added and stirred under room temperature for 5 hours. Diethylamine was evaporated under a reduced pressure and the residue was purified using a silica gel column chromatography (eluent: 1:20 mixture of ethyl acetate and hexane) to obtain 24 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. washThe extract was washed with 10 ml of saturated 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, 1.5 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: 1:20 mixture of ethyl acetate and hexane)

Sources & evidence

ORD record
ord-01791dcac5704ae2b99211fb1b6e39a4
Source dataset
uspto-grants-2001_11
Patent number
US06323353B1

Reaction notes

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