Triethylamine → HCID 60152049, compound

HRID 2404590Notes

Reaction equation

HRID 2404590 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH:11]([C:12]2[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=2)[CH2:10][CH:9]2[CH2:19][CH:6]1[CH2:7][CH2:8]2)[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]([C:12]2[CH:13]=[C:14]([O:18][C:22](=[O:23])[C:21]([CH3:26])([CH3:25])[CH3:20])[CH:15]=[CH:16][CH:17]=2)[CH2:10][CH:9]2[CH2:19][CH:6]1[CH2:7][CH2:8]2)[CH3:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 60151906HCID 60151906, compound

Product 1

HCID 60152049HCID 60152049, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stir a mixture of 3-(2-dimethylaminomethyl-bicyclo[3.2.1]oct-3-yl)-phenol (200 mg, 0.772 mmol), 2,2-dimethyl-propionyl chloride (111.6 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 reduced pressure, and purify the residue by preparative TLC to afford 2,2-dimethyl-propionic acid 3-(2-dimethylaminomethyl-bicyclo[3.2.1]oct-3-yl)-phenyl ester as white solid (217 mg, Yield: 81.9%). MS (m/z): 344 (M+1). 1H NMR (400 MHz, Methanol-d4) δ 7.36-7.40 (t, J=13.6, 1H), 7.19-7.21 (d, J=7.2, 1H), 7.03 (s, 1H), 6.92-6.94 (d, J=8.0, 1H), 2.97-3.03 (t, J=23.6, 1H), 2.49-2.68 (m, 6H), 2.40-2.44 (d, J=13.2, 1H), 2.35 (s, 2H), 2.17-2.21 (m, 2H), 1.60-1.84 (m, 8H), 1.37 (s, 9H).

Workup

  1. concentrationConcentrate the mixture under reduced pressure
  2. custompurify the residue by preparative TLC

Sources & evidence

ORD record
ord-1788aab25b164cc68258a7e8bcc7ea22
Source dataset
uspto-grants-2014_08
Patent number
US08802728B2

Reaction notes

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