Methanol → N-(3-Methoxy-2-methylphenyl)-tricyclo[3.3.1.13,7]decane-1-acetamide

HRID 1066255Notes

Reaction equation

HRID 1066255 reaction equation
N(C(OCC)=O)=N[C:3](OCC)=O.[OH:13][C:14]1[C:15]([CH3:34])=[C:16]([NH:20][C:21](=[O:33])[CH2:22][C:23]23[CH2:32][CH:27]4[CH2:28][CH:29]([CH2:31][CH:25]([CH2:26]4)[CH2:24]2)[CH2:30]3)[CH:17]=[CH:18][CH:19]=1.CO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.O1CCCC1>[CH3:3][O:13][C:14]1[C:15]([CH3:34])=[C:16]([NH:20][C:21](=[O:33])[CH2:22][C:23]23[CH2:32][CH:27]4[CH2:26][CH:25]([CH2:31][CH:29]([CH2:28]4)[CH2:30]2)[CH2:24]3)[CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 20660018N-(3-Hydroxy-2-methylphenyl)-tricyclo[3.3.1.13,7]decane-1-acetamide

Product 1

HCID 20660020N-(3-Methoxy-2-methylphenyl)-tricyclo[3.3.1.13,7]decane-1-acetamide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (0.20 ml) was added to a solution of N-(3-hydroxy-2-methylphenyl)-tricyclo[3.3.1.13,7]decane-1-acetamide (0.20 g, Example 26), methanol (0.10 ml) and triphenylphosphine (0.41 g) in toluene (10 ml) and tetrahydrofuran (5 ml). After 2 hours stirring at room temperature further triphenylphosphine (0.20 g) and diethyl azodicarboxylate (0.10 ml) were added and the solution stirred for 2 hours. The reaction mixture was concentrated under reduced pressure and the residue purified by silica gel to chromatography eluting with dichloromethane:ethyl acetate (19:1) to give the title compound as a colourless solid (0.20 g).

Workup

  1. additionwere added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue purified by silica gel to chromatography
  4. washeluting with dichloromethane:ethyl acetate (19:1)

Sources & evidence

ORD record
ord-e26195ac93e0429496f62f992b0c437b
Source dataset
uspto-grants-2001_06
Patent number
US06242470B1

Reaction notes

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