Boron tribromide → HCID 44595710, compound

HRID 1627060Notes

Reaction equation

HRID 1627060 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[C:15]2[O:16][CH2:17][CH2:18][C:14]=2[C:13]2[C@H:12]([CH2:19][CH2:20][NH:21][C:22](=[O:25])[CH2:23][CH3:24])[CH2:11][CH2:10][C:9]=2[CH:8]=1>C(Cl)Cl>[OH:6][C:7]1[C:15]2[O:16][CH2:17][CH2:18][C:14]=2[C:13]2[C@H:12]([CH2:19][CH2:20][NH:21][C:22](=[O:25])[CH2:23][CH3:24])[CH2:11][CH2:10][C:9]=2[CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67417683HCID 67417683, compound

Product 1

HCID 44595710HCID 44595710, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (6.92 mmol) was added dropwise into a solution of (S)—N-(2-[4-methoxy-1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl)propionamide (1.00 g. 3.46 mmol) in methylene chloride (15 mL) at about −50° C. The mixture was stirred for 2 hours at temperatures ranging from −50 to 0° C. Crushed ice was added and the mixture was stirred for further 2 hours at room temperature, followed by extracting with methanol-chloroform. The extracted solution was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of silica gel column chromatography (ethyl acetate) to afford the title compound (yield 320 mg, 34%) as a white powder. This compound is also referred to as metabolite 1.

Workup

  1. customranging from −50 to 0° C
  2. additionCrushed ice was added
  3. stirringthe mixture was stirred for further 2 hours at room temperature
  4. extractionby extracting with methanol-chloroform
  5. dry with materialThe extracted solution was dried over anhydrous magnesium sulfate
  6. distillationby distilling off the solvent under reduced pressure
  7. customThe residue was purified by means of silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-91108d327ea549428e811e3fd023f000
Source dataset
uspto-grants-2014_07
Patent number
US08785491B2

Reaction notes

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