Benzhydrylamine → HCID 86659010, compound

HRID 1942694Notes

Reaction equation

HRID 1942694 reaction equation
[Br:1][C:2]1[C:3]([CH2:13][CH3:14])=[C:4]([CH:8]([CH2:11]O)[CH2:9]O)[CH:5]=C[CH:7]=1.[C:15]1([CH:21]([NH2:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.CCN(C(C)C)C(C)C>CC#N>[CH:21]([N:28]1[CH2:9][CH:8]([C:4](=[CH2:5])[C:3]([CH2:13][CH3:14])=[C:2]([Br:1])[CH3:7])[CH2:11]1)([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 7036BenzhydrylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 58494111HCID 58494111, compound

Product 1

HCID 86659010HCID 86659010, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-(3-bromo-2-ethyl-phenyl)-propane-1,3-diol (D128) (8 g, 30.87 mmol) in 150 mL of CH3CN was added diphenylmethylamine (5.66 g, 30.87 mmol), trifluoromethanesulfonic anhydride, DIPEA at 0° C., and the reaction mixture was stirred for 12 hr at 70° C., then the reaction mixture was concentrated in vacuo. The residue was purified by column chromatography to afford 1-benzhydryl-3-(3-bromo-2-ethyl-1-methylene-but-2-enyl)-azetidine (D129) (3 g,).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-1476b6867fc44f87b5a1a1c86dc06d53
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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