Toluene → HCID 59883201, compound

HRID 1635602Notes

Reaction equation

HRID 1635602 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].C[B:24]1[O:29]B(C)OB(C)O1.[C:32]1(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]([O:29][CH3:32])[NH:1]2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 574072TrimethylboroxineHCID 12088879(R)-2-amino-2-cyclohexyl-1,1-diphenylethanol

Product 1

HCID 59883201HCID 59883201, compound

Procedure

A solution of (R)-2-amino-2-cyclohexyl-1,1-diphenylethanol, (2.95 g, 10 mmole) in toluene (34 mL) was distilled to remove (10 mL) of solvent. Additional toluene (17 mL) was added and a further 17 mL of solvent was distilled out. An additional 58 mL of toluene was added and a further 17 mL of solvent was distilled out. A further 17 mL of toluene was added followed by the addition of trimethylboroxine (0.93 mL, 6.68 mmole) at room temperature. The reaction mixture was kept at room temperature for 30 minutes and concentrated to a volume of 10 mL. Toluene (17 mL) was again added and a further 17 mL of distillate was distilled out. Additional toluene (17 mL) was added and the distillation was continued at atmospheric pressure until no more distillate was removed. Dry tetrahydrofuran was added to the residue to give a stock solution of the product (R)-4-cyclohexyl-5,5-diphenyl-2-methoxy-1,3,2-oxazaborolidine (3.2 g) in tetrahydrofuran (30 mL).

Workup

  1. customto remove (10 mL) of solvent
  2. additionAdditional toluene (17 mL) was added
  3. distillationa further 17 mL of solvent was distilled out
  4. additionAn additional 58 mL of toluene was added
  5. distillationa further 17 mL of solvent was distilled out
  6. additionA further 17 mL of toluene was added
  7. concentrationconcentrated to a volume of 10 mL
  8. additionToluene (17 mL) was again added
  9. distillationa further 17 mL of distillate was distilled out
  10. additionAdditional toluene (17 mL) was added
  11. distillationthe distillation
  12. customwas removed
  13. additionDry tetrahydrofuran was added to the residue

Sources & evidence

ORD record
ord-baf5b714030f4eb8a4a651cd753a831e
Source dataset
uspto-grants-2003_01
Patent number
US06509472B2

Reaction notes

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