Isopropanol → HCID 57948967, compound

HRID 1992275Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:15])[CH2:13][CH2:12][S:11][C:10]([NH2:14])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.CN(C)CC.[CH:21]([OH:24])(C)[CH3:22]>>[Br:1][C:2]1[CH:3]=[C:4]([C@:8]2([CH3:15])[CH2:13][CH2:12][S:11][C:10]([NH:14][C:21](=[O:24])[CH3:22])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 3776Isopropanol

HCID 11723Dimethylethylamine

HCID 57627869HCID 57627869, compound

Product 1

HCID 57948967HCID 57948967, compoundYield 35%

Procedure

4-(3-bromo-phenyl)-4-methyl-5,6-dihydro-4H-[1,3]thiazin-2-ylamine (20 g, 61 mmole) is purified by HPLC chiral separation [Column: 8×32 cm chiralpak AD; Eluent: 60:40:0.2 (isopropyl alcohol: heptanes: dimethylethylamine); Flow: 350 mL/min at UV 260 nm]. The second eluting isomer is isolated to provide the enantiomerically enriched title compound (35% Yield): MS (m/z): 327, 329 (M+1)

Workup

customThe second eluting isomer is isolated

Sources & evidence

ORD record: ord-f9955387c9a24d5b83c755150348ae30
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07648983B2

Reaction notes

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