Boron tribromide → HCID 21461153, compound

HRID 1941461Notes

Reaction equation

HRID 1941461 reaction equation
B(Br)(Br)Br.[CH:5]1([C:8]([N:10]2[CH2:15][CH2:14][CH:13]([CH:16]3[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([O:25]C)[CH:23]=4)[CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[O:9])[CH2:7][CH2:6]1>C(Cl)Cl>[CH:5]1([C:8]([N:10]2[CH2:15][CH2:14][CH:13]([CH:16]3[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([OH:25])[CH:23]=4)[CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[O:9])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 9817776HCID 9817776, compound

Product 1

HCID 21461153HCID 21461153, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 1M boron tribromide solution (3 mL, 3 mmol) was added at -78 ° C. to a solution of N-cyclopropylcarbonyl-4-(6-methoxy-indan-1-yl)piperidine (0.45 g, 1.5 mmol) in methylene chloride. After stirring for 18 h the reaction was quenched with water. The organic layer was separated and washed with 1N NaOH solution and concentrated in vacuo. The residue was stirred for 18 h with a mixture of methanol and 1N NaOH. The methanol was removed in vacuo and the solution was made acid with 1N HCl. The insolubles were collected by filtration to give 0.15 g product, mp 75°-82° C. Anal. Calc'd for C18H23NO2 ·0.3H2O: C, 74.35%; H, 8.18%; N, 4.82%. Found: C, 74.4%; H, 8.08%; N, 4.74%.

Workup

  1. customwas quenched with water
  2. customThe organic layer was separated
  3. washwashed with 1N NaOH solution
  4. concentrationconcentrated in vacuo
  5. stirringThe residue was stirred for 18 h with a mixture of methanol and 1N NaOH
  6. customThe methanol was removed in vacuo
  7. filtrationThe insolubles were collected by filtration

Sources & evidence

ORD record
ord-547c7b0f399a40368658fcdbe33e1fda
Source dataset
uspto-grants-1997_12
Patent number
US05703239

Reaction notes

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