2,6-Lutidine → HCID 57507760, compound

HRID 2074300Notes

Reaction equation

HRID 2074300 reaction equation
O[CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)=[CH:9][CH:8]=1)=[O:6].C(Br)(Br)(Br)Br.N1C(C)=CC=CC=1C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[N:4]1([C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][CH:15]3[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[CH2:19][CH2:20]3)=[CH:11][CH:12]=2)=[O:6])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 57507759HCID 57507759, compound

Product 1

HCID 57507760HCID 57507760, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 4-[2-(4-{[(2-hydroxyethyl)amino]carbonyl}phenyl)ethyl]piperidine-1-carboxylate (280 mg), carbon tetrabromide (247 mg) and 2,6-lutidine (103 μl) were dissolved in dichloromethane (5.6 ml), and under ice cooling, triphenylphosphine (195 mg) was added thereto, followed by stirring at room temperature for 3 hours. The solvent was evaporated, and the residue was purified by silica gel column chromatography (eluent: hexane:EtOAc=3:7 (v/v)) to obtain tert-butyl 4-{2-[4-(1-aziridinylcarbonyl)phenyl]ethyl}-1-piperidinecarboxylate (136 mg) as a colorless oil.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by silica gel column chromatography (eluent: hexane:EtOAc=3:7 (v/v))

Sources & evidence

ORD record
ord-6c06ec172fb64e1bbab12bdb1b1f3973
Source dataset
uspto-grants-2011_04
Patent number
US07919495B2

Reaction notes

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