Boron trifluoride etherate → HCID 53847367, compound

HRID 1195908Notes

Reaction equation

HRID 1195908 reaction equation
C([O:8][NH:9][CH:10]([C:12]1[N:13]([CH3:23])[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:15][CH:16]=1)[CH3:11])C1C=CC=CC=1.C([Li])(C)(C)C.[NH:29]1[CH:33]=CC=[CH:30]1.B(F)(F)F.CC[O:40]CC.[NH4+].[Cl-]>C1COCC1>[OH:8][N:9]([CH:10]([C:12]1[N:13]([CH3:23])[C:14]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:15][CH:16]=1)[CH3:11])[C:30]([NH:29][CH3:33])=[O:40]

Participants

7

Reactant 5

HCID 8000Boron trifluoride etherateHCID 8027PyrroleHCID 25517Ammonium ChlorideHCID 57169087HCID 57169087, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 53847367HCID 53847367, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Benzyloxy-1-(1-methyl-5-phenylpyrrol-2-yl)ethylamine. t-Butyl lithium (4.1 ml, 1.7M in hexanes) was added to a solution of the pyrrole prepared as in step a, above (1.0 g, 6.4 mmole) in THF (25 mL) at -78° C. After stirring for 30 minutes, boron trifluoride etherate (0.99 g, 7.0 mmole) was added followed by O-benzyl acetaldehyde oxime (1.0 g, 7.0 mmole). The mixture was stirred for 15 min, saturated NH4Cl solution was added, and the mixture was allowed to warm to room temperature. The aqueous phase was washed twice with brine, dried over MgSO4 and concentrated. The residue was chromatographed on 100 g of silica gel eluting with 20% ether in hexanes to give 0.34 g of the desired product.

Workup

  1. stirringThe mixture was stirred for 15 min
  2. washThe aqueous phase was washed twice with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed on 100 g of silica gel eluting with 20% ether in hexanes

Sources & evidence

ORD record
ord-00360fd929fa4e22b25efcb9bb966096
Source dataset
uspto-grants-1992_05
Patent number
US05112848

Reaction notes

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