Methanol → N-Desethyloxybutynin

HRID 1489224Notes

Reaction equation

HRID 1489224 reaction equation
[CH:1]1([C:7]([OH:33])([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:8]([O:10][CH2:11][C:12]#[C:13][CH2:14][N:15](CC2C=CC(OC)=CC=2)[CH2:16][CH3:17])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)OC(Cl)C.CO>ClC(Cl)C>[CH:27]1([C:7]([OH:33])([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]([O:10][CH2:11][C:12]#[C:13][CH2:14][NH:15][CH2:16][CH3:17])=[O:9])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 887MethanolHCID 5213051-Chloroethyl chloroformateHCID 50442254-[Ethyl-[(4-methoxyphenyl)methyl]amino]but-2-ynyl 2-cyclohexyl-2-hydroxy-2-phenylacetate

Product 1

HCID 133577N-Desethyloxybutynin

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

reacting said 4-[N-ethyl-(4-methoxyphenyl)methylamino]-2-butynyl α-cyclohexyl-α-hydroxybenzeneacetate sequentially with α-chloroethyl carbonochloridate in dichloroethane, followed by methanol to produce 4-(ethylamino)-2-butynyl α-cyclohexyl-α-hydroxybenzeneacetate (desethyloxybutyin).

Sources & evidence

ORD record
ord-08a020ff58324287ba2074fca30cda7b
Source dataset
uspto-grants-1997_10
Patent number
US05677346

Reaction notes

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