Dichloromethane → HCID 70358081, compound

HRID 1762589Notes

Reaction equation

HRID 1762589 reaction equation
Cl.[CH2:2]([O:4][C:5]([C:7]1[CH2:8][N:9]([CH2:14][C:15]2[C:18]3[CH:19]=[C:20]([O:23]C)[CH:21]=[CH:22][C:17]=3[CH:16]=2)[CH2:10][CH2:11][C:12]=1[OH:13])=[O:6])[CH3:3].ClCCl.B(Br)(Br)[Br:29]>C(O)C>[BrH:29].[CH2:2]([O:4][C:5]([C:7]1[CH2:8][N:9]([CH2:14][C:15]2[C:18]3[CH:19]=[C:20]([OH:23])[CH:21]=[CH:22][C:17]=3[CH:16]=2)[CH2:10][CH2:11][C:12]=1[OH:13])=[O:6])[CH3:3].[BrH:29].[CH2:2]([O:4][C:5]([CH:7]1[C:12](=[O:13])[CH2:11][CH2:10][N:9]([CH2:14][C:15]2[C:18]3[CH:19]=[C:20]([OH:23])[CH:21]=[CH:22][C:17]=3[CH:16]=2)[CH2:8]1)=[O:6])[CH3:3]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 70358074HCID 70358074, compound

Product 2

HCID 70358081HCID 70358081, compoundHCID 70358213HCID 70358213, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2 g (5.7 mmol) of 4-hydroxy-1-[(5-methoxybenzocyclobuten-1-yl)methyl]-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester hydrochloride are introduced, at -80° C. under argon, into 80 ml of dichloromethane. While stirring, 1.08 ml (11.3 mmol) of boron tribromide are metered in. After 30 minutes at -80° C., the reaction mixture is gradually heated to +5° C. over a period of 2 hours while stirring. 40 ml of ethanol are then cautiously added and the whole is subsequently concentrated under a water-jet vacuum. The residue is dissolved in 150 ml of ethanol and again concentrated by evaporation under a water-jet vacuum. This procedure is repeated twice more. The resulting residue is then crystallised from ethanol/diethyl ether. 4-hydroxy-1-[(5-hydroxybenzocyclobuten-1-yl)methyl]-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester hydrobromide and 1-[(5-hydroxybenzocyclobuten-1-yl)methyl]-4-oxo-piperidine-3-carboxylic acid ethyl ester hydrobromide of m.p. 192°-194° C. are obtained.

Workup

  1. temperaturethe reaction mixture is gradually heated to +5° C. over a period of 2 hours
  2. stirringwhile stirring
  3. concentrationthe whole is subsequently concentrated under a water-jet vacuum
  4. dissolutionThe residue is dissolved in 150 ml of ethanol
  5. concentrationagain concentrated by evaporation under a water-jet vacuum
  6. customThe resulting residue is then crystallised from ethanol/diethyl ether

Sources & evidence

ORD record
ord-9d3dd72390c241929f4e670043e68646
Source dataset
uspto-grants-1989_05
Patent number
US04833169

Reaction notes

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