Boron tribromide → HCID 18367303, compound

HRID 1741403Notes

Reaction equation

HRID 1741403 reaction equation
B(Br)(Br)Br.[C:5]1([C:11]2[N:12]=[C:13]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][N:23]3[CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([O:35]C)[CH:30]=3)[O:14][C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(Cl)Cl>[C:5]1([C:11]2[N:12]=[C:13]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][N:23]3[CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=3)[O:14][C:15]=2[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 18367235HCID 18367235, compound

Product 1

HCID 18367303HCID 18367303, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1.0 M solution of boron tribromide in methylene chloride (2.08 ml) was added dropwise to a solution of 2-(4,5-diphenyl-2-oxazolyl)-1-(3-methoxybenzyl)piperidine (440 mg) in methylene chloride (2.5 ml) under ice cooling. The resulting mixture was stirred at the same temperature for 3 hours and partitioned between ethyl acetate and aqueous sodium bicarbonate. The organic layer was washed with water and brine, dried over MgSO4, and evaporated in vacuo. The residue was chromatographed over silica gel to afford 2-(4,5-diphenyl-2-oxazolyl)-1-(3-hydroxybenzyl)piperidine (388 mg) as a pale yellow powder. FABMS (m/z): 410 (M+) mp: 204.7-208.3° C. IR (Film): 1600, 1585, 1255 cm-1NMR (CDCl3, δ): 1.2-1.95 (6H, m), 2.0-2.25 (1H, m), 3.05-3.11 (1H, m), 3.25-3.37 (1H, m), 3.73-3.81 (2H, m), 6.71-6.83 (3H, m), 7.13 (1H, q, J=7.7 Hz), 7.25-7.48 (11H, m)

Workup

  1. custompartitioned between ethyl acetate and aqueous sodium bicarbonate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-026cae274b7d42c39fe393cf77b4d571
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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