Pyridine → HCID 57107979, compound

HRID 1682320Notes

Reaction equation

HRID 1682320 reaction equation
N1C=CC=CC=1.[C:7]([O:11][C:12]([N:14]1[C@H:18]([CH:19]=[CH:20][CH2:21][CH2:22][CH2:23]O)[CH2:17][O:16][C:15]1([CH3:26])[CH3:25])=[O:13])([CH3:10])([CH3:9])[CH3:8].[Br:27]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[C:7]([O:11][C:12]([N:14]1[C@H:18]([CH:19]=[CH:20][CH2:21][CH2:22][CH2:23][Br:27])[CH2:17][O:16][C:15]1([CH3:26])[CH3:25])=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 1049PyridineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 57309346HCID 57309346, compound

Product 1

HCID 57107979HCID 57107979, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7 ml of pyridine are added dropwise at 0° to a solution of 18.5 g of alcohol 3 according to c), 28.2 g of tetrabromomethane and 22.3 g of triphenylphosphine in 600 ml of dichloromethane. The mixture is stirred at 0°-2° for 12 hours, concentrated by evaporation, taken up in 150 ml of ethyl acetate, filtered, concentrated to 50 ml and chromatographed on 200 g of silica gel. Elution with hexane/ethyl acetate 10:1 yields 19.9 g of bromide 4, [α]D =-18.9° (c=1, CHCl3); C15H26NO3Br; calculated: C 51.73%, H 7.53%, N 4.02%, Br 22.94%; found: C 51.7%, H 7.7%, N 4.2%, Br 23.0%.

Workup

  1. concentrationconcentrated by evaporation
  2. filtrationfiltered
  3. concentrationconcentrated to 50 ml
  4. customchromatographed on 200 g of silica gel
  5. washElution with hexane/ethyl acetate 10:1

Sources & evidence

ORD record
ord-ca5cd3baaefd40a7889c09fa6344339b
Source dataset
uspto-grants-1992_12
Patent number
US05175344

Reaction notes

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