Triethylamine → HCID 60152193, compound

HRID 2404586Notes

Reaction equation

HRID 2404586 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH:11]2[CH2:12][CH:8]([CH2:9][CH2:10]2)[CH:7]=[C:6]1[C:13]1[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=1)[CH3:3].[CH3:20][C:21]([CH3:26])([CH3:25])[C:22](Cl)=[O:23].C(N(CC)CC)C>C(Cl)Cl>[CH3:3][N:2]([CH2:4][CH:5]1[CH:11]2[CH2:12][CH:8]([CH2:9][CH2:10]2)[CH:7]=[C:6]1[C:13]1[CH:14]=[C:15]([O:19][C:22](=[O:23])[C:21]([CH3:26])([CH3:25])[CH3:20])[CH:16]=[CH:17][CH:18]=1)[CH3:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 60151763HCID 60151763, compound

Product 1

HCID 60152193HCID 60152193, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stir a mixture of 3-(4-dimethylaminomethyl-bicyclo[3.2.1]oct-2-en-3-yl)-phenol (200 mg, 0.778 mmol), 2,2-dimethyl-propionyl chloride (111 mg, 0.927 mmol) and triethyl amine (234 mg, 2.316 mmol) in CH2Cl2 (40 mL) at ambient temperature for 12 hours. Concentrate the mixture under vacuum, and purify the residue by Preparative TLC to give 2,2-dimethyl-propionic acid 3-(4-dimethylaminomethyl-bicyclo[3.2.1]oct-2-en-3-yl)-phenyl ester as white solid (232 mg, Yield: 87.5%). MS (m/z): 342 (M+1). 1H NMR (400 MHz, Methanol-d4) δ 7.29-7.32 (t, J=15.6 Hz, 1H), 7.06-7.08 (d, J=7.6, 1H), 6.88-6.90 (d, J1=8.0, J2=1.6, 1H), 6.84-6.85 (t, J=3.6, 1H), 6.05-6.07 (d, J=6.8, 1H), 3.22-3.32 (m, 1H), 2.52-2.60 (m, 1H), 2.62-2.63 (m, 1H), 2.37-2.41 (m, 1H), 2.17 (s, 6H), 2.07-2.14 (m, 1H), 1.71-1.85 (m, 6H), 1.37 (s, 9H).

Workup

  1. concentrationConcentrate the mixture under vacuum
  2. custompurify the residue by Preparative TLC

Sources & evidence

ORD record
ord-1ecc43b812b3494ba88294ab9ac497d1
Source dataset
uspto-grants-2014_08
Patent number
US08802728B2

Reaction notes

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