Diethyl Ether → HCID 69133464, compound

HRID 2116877Notes

Reaction equation

[CH:1]([N:4]([CH:22]([CH3:24])[CH3:23])[CH2:5][CH2:6][C@@H:7]([C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[OH:21])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2].CCOCC.[C:30](Cl)(=[O:34])[CH2:31][CH2:32][CH3:33]>>[C:30]([O:21][C:15]1[CH:16]=[CH:17][C:18]([CH3:20])=[CH:19][C:14]=1[C@@H:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:6][CH2:5][N:4]([CH:1]([CH3:3])[CH3:2])[CH:22]([CH3:24])[CH3:23])(=[O:34])[CH2:31][CH2:32][CH3:33]

Participants

Reactant 3

HCID 3283Diethyl Ether

HCID 8855Butyryl chloride

HCID 443879Tolterodine

Product 1

HCID 69133464HCID 69133464, compound

Procedure

A solution of 2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-methylphenol (1.0 g) in butyryl chloride (5 ml) is heated under reflux for 90 min. Ether is added, and the precipitate of 2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-methylphenyl butyrate hydrochloride is filtered off; mp 116-119° C. Anal Calcd for C26H37NO2.HCl: C, 72.28; H, 8.86; Cl, 8.21; N, 3.24. Found: C, 72.25; H, 8.71; Cl, 8.17; N, 3.25. [α]D (c=1, MeOH) +20°.

Workup

temperatureunder reflux for 90 min
filtrationthe precipitate of 2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-methylphenyl butyrate hydrochloride is filtered off
custom[α]D (c=1, MeOH) +20°

Sources & evidence

ORD record: ord-7dc30dd980e3417cab44e0bba84bf036
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07439397B2

Reaction notes

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