Boron tribromide → HCID 86756987, compound

HRID 1066249Notes

Reaction equation

HRID 1066249 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:22])[CH2:11][C:12]23[CH2:21][CH:16]4[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]4)[CH2:13]2)[CH2:19]3)=[C:5]([CH3:23])[CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([C:10](=[O:22])[CH2:11][C:12]23[CH2:21][CH:16]4[CH2:15][CH:14]([CH2:20][CH:18]([CH2:17]4)[CH2:19]2)[CH2:13]3)[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[C:5]([CH3:23])[CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 20660022HCID 20660022, compound

Product 1

HCID 86756987HCID 86756987, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-(4-Methoxy-2-methylphenyl)-tricyclo[3.3.1.13,7]decane-1-acetamide from Example 20 (1.20 g) in dichloromethane (50 ml) at −78° C. was added boron tribromide (4 ml of a 1.0M solution in dichloromethane) under an inert atmosphere. The reaction mixture was stirred for 24 hours and then warmed to ambient temperature and washed with brine. The organic layer was then dried over magnesium sulphate (MgSO4) and concentrated under reduced pressure to yield a residue which was purified by silica gel chromatography eluting with iso-hexane/diethyl ether (1:1) to give the ititle compound as a white solid. (0.54 g).

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was then dried over magnesium sulphate (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customto yield a residue which
  5. customwas purified by silica gel chromatography
  6. washeluting with iso-hexane/diethyl ether (1:1)

Sources & evidence

ORD record
ord-462a2748e0244a9599041e66e8521cc4
Source dataset
uspto-grants-2001_06
Patent number
US06242470B1

Reaction notes

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