Trimethylboroxine → HCID 59883199, compound

HRID 1635601Notes

Reaction equation

HRID 1635601 reaction equation
[NH2:1][C@H:2]([CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[C:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].[CH3:23][B:24]1OB(C)OB(C)O1>C1(C)C=CC=CC=1>[CH:17]1([C@@H:2]2[C:3]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[O:4][B:24]([CH3:23])[NH:1]2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 574072TrimethylboroxineHCID 12088879(R)-2-amino-2-cyclohexyl-1,1-diphenylethanol

Product 1

HCID 59883199HCID 59883199, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

(R)-2-amino-2-cyclohexyl-1,1-diphenylethanol (2.95 g, 10 mmole) and toluene (60 mL) were charged to a 100 mL single neck flask fitted with a Dean and Stark trap, which was then flushed with nitrogen. The mixture was concentrated by distillation at atmospheric pressure to a volume of 30 mL. Toluene (30 mL) was then added and the mixture was concentrated again by distillation to 30 mL. Toluene (30 mL) was again added and the mixture was concentrated again by distillation to 30 mL. The reaction mixture was cooled to room temperature, trimethylboroxine (0.94 mL, 6.7 mmol) was added and the reaction mixture was stirred at room temperature for 16 hours. Toluene (20 mL) was added and 30 mL of solvent was distilled out. More toluene (30 mL) was added and 30 mL more of the solvent was distilled out. Once again, more toluene (30 mL) was added and then all the solvent was removed by distillation to give (R)-4-cyclohexyl-5,5-diphenyl-2-methyl- 1,3,2-oxazaborolidine.

Workup

  1. customfitted with a Dean and Stark trap, which
  2. customwas then flushed with nitrogen
  3. concentrationThe mixture was concentrated by distillation at atmospheric pressure to a volume of 30 mL
  4. additionToluene (30 mL) was then added
  5. concentrationthe mixture was concentrated again by distillation to 30 mL
  6. additionToluene (30 mL) was again added
  7. concentrationthe mixture was concentrated again by distillation to 30 mL
  8. distillation30 mL of solvent was distilled out
  9. additionMore toluene (30 mL) was added
  10. distillation30 mL more of the solvent was distilled out
  11. additionOnce again, more toluene (30 mL) was added
  12. customall the solvent was removed by distillation

Sources & evidence

ORD record
ord-6ce246e887f24afa9410a666cf301eb8
Source dataset
uspto-grants-2003_01
Patent number
US06509472B2

Reaction notes

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