Water → HCID 86694781, compound

HRID 2404587Notes

Reaction equation

HRID 2404587 reaction equation
O.C[Si]([Cl:6])(C)C.[CH3:7][N:8]([CH2:10][CH:11]1[CH:17]2[CH2:18][CH:14]([CH2:15][CH2:16]2)[CH:13]=[C:12]1[C:19]1[CH:20]=[C:21]([O:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])[CH:22]=[CH:23][CH:24]=1)[CH3:9]>CC(=O)CC>[ClH:6].[CH3:9][N:8]([CH2:10][CH:11]1[CH:17]2[CH2:18][CH:14]([CH2:15][CH2:16]2)[CH:13]=[C:12]1[C:19]1[CH:20]=[C:21]([O:25][C:26](=[O:31])[C:27]([CH3:29])([CH3:28])[CH3:30])[CH:22]=[CH:23][CH:24]=1)[CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 60152193HCID 60152193, compound

Product 1

HCID 86694781HCID 86694781, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Add H2O (18 mg, 1 mmol) and TMSCl (75 mg, 0.69 mmol) to a solution of 2,2-dimethyl-propionic acid 3-(4-dimethylaminomethyl-bicyclo[3.2.1]oct-2-en-3-yl)-phenyl ester (197 mg, 0.58 mmol) in 2-butanone (70 mL). Stir the reaction mixture at ambient temperature for 2 hours. Evaporate the mixture under vacuum to afford 2,2-dimethyl-propionic acid 3-(4-dimethylaminomethyl-bicyclo[3.2.1]oct-2-en-3-yl)-phenyl ester hydrochloride as white solid (219 mg, Yield: 100%). 1H NMR (400 MHz, Methanol-d4) δ 7.38-7.42 (t, J=16.4, 1H), 7.13-7.15 (d, J1=7.2, J2=0.8, 1H), 6.96-6.98 (m, 2H), 6.21-6.23 (d, J=6.8, 1H), 3.68-3.71 (d, J=12.0, 1H), 3.16-3.23 (t, J=25.6, 1H), 2.99-3.00 (m, 1H), 2.88-2.92 (d, J=14.8, 6H), 2.65 (m, 1H), 2.60 (m, 1H), 1.95-1.98 (m, 1H), 1.82-1.86 (m, 5H), 1.37 (s, 9H).

Workup

  1. customEvaporate the mixture under vacuum

Sources & evidence

ORD record
ord-6c7d988cc44e42bbb4e758701b3bea63
Source dataset
uspto-grants-2014_08
Patent number
US08802728B2

Reaction notes

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