Trimethylboroxine → (3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaborole

HRID 1004491

Reaction equation

HRID 1004491 reaction equation
[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C@@H:9]2[CH2:13][CH2:12][CH2:11][NH:10]2)[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:20][B:21]1OB(C)OB(C)O1>C1(C)C=CC=CC=1>[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:8][B:21]([CH3:20])[N:10]3[CH2:11][CH2:12][CH2:13][C@@H:9]23)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 574072TrimethylboroxineHCID 27248992-Pyrrolidinemethanol, alpha,alpha-diphenyl-, (S)-

Product 1

HCID 2734713(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaboroleYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under argon stream, to a solution of (S)-α,α-diphenyl-2-pyrrolidine methanol (3 g, 11.8 mmol) in dry toluene (90 ml) was added trimethyl boroxine (1.13 ml, 8.0 mmol), followed by stirring for 1.5 hours. After the argon stream was stopped and the toluene (22.5 ml) was recovered under normal pressures on an oil bath at 140° C., dry toluene (22.5 ml) was added. Furthermore, after this recovery operation was repeated twice, the resultant product was concentrated under normal pressures, and subsequently under a reduced pressure, to thereby obtain the titled compound as a colorless crystalline.

Workup

  1. customthe toluene (22.5 ml) was recovered under normal pressures on an oil bath at 140° C.
  2. additiondry toluene (22.5 ml) was added
  3. concentrationthe resultant product was concentrated under normal pressures

Sources & evidence

ORD record
ord-4a63ecdf7488425e96ba5e72240b0c99
Source dataset
uspto-grants-2000_04
Patent number
US06049009

Linked notes

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