Diethyl Ether → N-(5-Hydroxy-2-methylphenyl)-tricyclo[3.3.1.13,7]decane-1-acetamide

HRID 1066241Notes

Reaction equation

HRID 1066241 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:23])=[C:7]([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)[CH:8]=1.B(Br)(Br)Br.C(OCC)C>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:23])=[C:7]([NH: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)[CH:8]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 25134Boron tribromideHCID 9926842N-(5-Methoxy-2-methylphenyl)-tricyclo[3.3.1.13,7]decane-1-acetamide

Product 1

HCID 9904389N-(5-Hydroxy-2-methylphenyl)-tricyclo[3.3.1.13,7]decane-1-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-(5-methoxy-2-methylphenyl)-tricyclo[3.3.1.13,7]decane-1-acetamide prepared as described in Example 5 (1.00 g) in dichloromethane (20 ml), was added boron tribromide (4 ml of a 1.0M solution in dichloromethane) at −78° C. 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 dried over magnesium sulphate (MgSO4) and concentrated under reduced pressure to yield a residue. Trituration with diethyl ether gave a solid (0.335 g). A portion of this material (0.050 g) was further purified by Supercritical Fluid chromatography using a Cyano column, eluting with a gradient of methanol in supercritical carbon dioxide to give the title compound as a white solid (0.030 g).

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried over magnesium sulphate (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customto yield a residue

Sources & evidence

ORD record
ord-e412a27abe144424b613f6a2950aed0c
Source dataset
uspto-grants-2001_06
Patent number
US06242470B1

Reaction notes

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