Boron trifluoride etherate → HCID 86592625, compound

HRID 8230Notes

Reaction equation

HRID 8230 reaction equation
B(F)(F)F.CCOCC.[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[N:21]=2)=O)=[CH:13][CH:12]=1.[NH2:27][N:28]1[C@@H:32]([CH2:33][O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:31][CH2:30][C:29]1=[O:42]>O1CCCC1>[CH2:35]([O:34][CH2:33][C@@H:32]1[N:28]([N:27]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[N:21]=2)[CH2:17][C:14]2[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=2)[C:29](=[O:42])[CH2:30][CH2:31]1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 219925362-(4-Fluorophenyl)-1-(6-methylpyridin-2-yl)ethanoneHCID 69364615(R)-1-amino-5-benzyloxymethyl-pyrrolidin-2-one

Product 1

HCID 86592625HCID 86592625, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Boron trifluoride etherate (0.25 mL, 1.98 mmol) is added to a solution of 2-(4-fluoro-phenyl)-1-(6-methyl-pyridin-2-yl)-ethanone (0.45 g, 1.98 mmol) in tetrahydrofuran (6.6 mL) under nitrogen and stirred for 30 min. A solution of (R)-1-amino-5-benzyloxymethyl-pyrrolidin-2-one (0.43 g, 1.98 mmol) in tetrahydrofuran (1.0 mL) is added and the resulting mixture is stirred for 1 h. The mixture is concentrated in vacuo and the residue chromatographed on a SiO2 column (30% ethyl acetate/hexanes) to yield the title compound, 380 mg (45%), as a yellow foam.

Workup

  1. stirringthe resulting mixture is stirred for 1 h
  2. concentrationThe mixture is concentrated in vacuo
  3. customthe residue chromatographed on a SiO2 column (30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f20cb3d9c17f4dcbbbca7c8f90a35e53
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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