Water → HCID 68291173, compound

HRID 2404591Notes

Reaction equation

HRID 2404591 reaction equation
O.C[Si]([Cl:6])(C)C.[CH3:7][N:8]([CH2:10][CH:11]1[CH:17]([C:18]2[CH:19]=[C:20]([O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])[CH:21]=[CH:22][CH:23]=2)[CH2:16][CH:15]2[CH2:31][CH:12]1[CH2:13][CH2:14]2)[CH3:9]>CC(=O)CC>[ClH:6].[CH3:7][N:8]([CH2:10][CH:11]1[CH:17]([C:18]2[CH:19]=[C:20]([O:24][C:25](=[O:30])[C:26]([CH3:27])([CH3:29])[CH3:28])[CH:21]=[CH:22][CH:23]=2)[CH2:16][CH:15]2[CH2:31][CH:12]1[CH2:13][CH2:14]2)[CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 60152049HCID 60152049, compound

Product 1

HCID 68291173HCID 68291173, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Add H2O (9 mg, 0.5 mmol) and TMSCl (39 mg, 0.357 mmol) to a solution of 2,2-dimethyl-propionic acid 3-(2-dimethylaminomethyl-bicyclo[3.2.1]oct-3-yl)-phenyl ester (102 mg, 0.297 mmol) in 2-butanone (50 mL). Then stir the reaction mixture at ambient temperature for 4 hours. Evaporate the mixture under vacuum to give 2,2-dimethyl-propionic acid 3-(2-dimethylaminomethyl-bicyclo[3.2.1]oct-3-yl)-phenyl ester hydrochloride as white solid (112 mg, Yield: 100%). 1H NMR (400 MHz, Methanol-d4) δ 7.38-7.42 (t, J=15.6, 1H), 7.20-7.22 (d, J=7.6, 1H), 7.05 (s, 1H), 6.94-6.96 (m, 1H), 3.08-3.14 (m, 1H), 2.79 (s, 3H), 2.66 (s, 3H), 2.53-2.57 (m, 2H), 2.36 (s, 2H), 2.23 (m, 1H), 1.61-1.85 (m, 8H), 1.39 (s, 9H).

Workup

  1. customEvaporate the mixture under vacuum

Sources & evidence

ORD record
ord-f5fed3f1d3c04a359c4a76ece0d17f50
Source dataset
uspto-grants-2014_08
Patent number
US08802728B2

Reaction notes

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