Boron tribromide → HCID 136413217, compound

HRID 470628Notes

Reaction equation

HRID 470628 reaction equation
B(Br)(Br)Br.[CH2:5]([N:12]1[CH2:17][CH2:16][CH:15]([CH2:18][C:19]2[N:23]=[C:22]([CH:24]=[CH:25][C:26]3[CH:31]=[CH:30][C:29]([O:32]C)=[C:28]([O:34]C)[CH:27]=3)[O:21][N:20]=2)[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>ClCCl>[CH2:5]([N:12]1[CH2:17][CH2:16][CH:15]([CH2:18][C:19]2[N:23]=[C:22]([CH:24]=[CH:25][C:26]3[CH:27]=[C:28]([OH:34])[C:29]([OH:32])=[CH:30][CH:31]=3)[O:21][N:20]=2)[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67395995HCID 67395995, compound2×

Product 1

HCID 136413217HCID 136413217, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (0.056 mL, 0,595 mmol) was added drop wise to a cooled solution of 1-benzyl-4-{5-[2-(3,4-dimethoxy-phenyl)-vinyl]-[1,2,4]oxadiazol-3-ylmethyl}-piperidine (compound of Example 30; 0.05 g, 0.12 mol) in dichloromethane (3 mL) at −78° C. The reaction mixture was warmed to room temperature and stirred for 6 h. The reaction mixture was quenched with methanol (2 mL) and the organic solvent was evaporated. The residue was suspended in methanolic ammonia (2 mL) and the undissolved solid was filtered. The filtrate was evaporated to obtain a crude product, which was purified by column chromatography (silica gel, 3% methanol in chloroform) to afford the title compound.

Workup

  1. customThe reaction mixture was quenched with methanol (2 mL)
  2. customthe organic solvent was evaporated
  3. filtrationthe undissolved solid was filtered
  4. customThe filtrate was evaporated
  5. customto obtain a crude product, which
  6. customwas purified by column chromatography (silica gel, 3% methanol in chloroform)

Sources & evidence

ORD record
ord-eacf4603207c473896b3fa49751fe063
Source dataset
uspto-grants-2014_01
Patent number
US08629277B2

Reaction notes

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