Hydrochloric Acid → (Z)-(S)-[3-(3-methoxy-phenyl)-2-methyl-pent-3-enyl]-dimethyl-amine

HRID 2369478Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]([CH2:16][CH3:17])[CH:10]([CH3:15])[CH2:11][N:12]([CH3:14])[CH3:13])[CH:6]=[CH:7][CH:8]=1.Cl>>[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[C:9](=[CH:16]\[CH3:17])/[C@H:10]([CH3:15])[CH2:11][N:12]([CH3:14])[CH3:13])[CH:6]=[CH:7][CH:8]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 223770203-(3-methoxy-phenyl)-N,N,2-trimethyl pentylamine

Product 1

HCID 11425684(Z)-(S)-[3-(3-methoxy-phenyl)-2-methyl-pent-3-enyl]-dimethyl-amine

Procedure

The yield of [3-(3-methoxy-phenyl)-2-methyl-pentyl]-dimethyl-amine; hydrochloride (3) was >96% with a ratio of the enantiomer (−)-(2R,3R) to the diastereoisomer (−)-(2R,3S) of 76:24. The (−)-(2R,3R) enantiomer is preferably used as an active ingredient in medicaments.

Sources & evidence

ORD record: ord-9e75a225b2f543568d569e62b20eeb79
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08704002B2

Reaction notes

Loading…