(-)-Epichlorohydrin → Epichlorohydrin

HRID 2102579Notes

Reaction equation

HRID 2102579 reaction equation
[CH2:1]([CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH:12]([OH:25])[CH2:13][N:14]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[O:17][CH2:16][C:15]2=[O:24])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[CH2:26]([C@@H:28]1[O:30][CH2:29]1)[Cl:27]>>[CH2:26]([CH:28]1[O:30][CH2:29]1)[Cl:27].[CH2:1]([CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH:12]([OH:25])[CH2:13][N:14]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[O:17][CH2:16][C:15]2=[O:24])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 2734062(-)-EpichlorohydrinHCID 10125981HCID 10125981, compound

Product 2

HCID 7835EpichlorohydrinHCID 10125981HCID 10125981, compound

Procedure

Following the method outlined above for (R/S)-4-[3-(4-butylpiperidin-1-yl)-2-hydroxypropyl]-4H-benzo[1,4]oxazin-3-one using (R)-(−)-epichlorohydrine (97% ee), (instead of racemic epichlorohydrin, gave the title compound. The optical purity was determined by HPLC analysis (Chiralpak AD, 250×4.6, 5 μm; hexane/i-PrOH/diethylamine 95:4.7:0.3, 0.5 mL/min) to be 96.3% ee. ([α]D20=−6, c=0.5, EtOH). 1H NMR, 13C NMR and HPLC-MS spectral data were identical to those of the racemic compound.

Sources & evidence

ORD record
ord-2c295529cb2541e8a5ca508de8cab9db
Source dataset
uspto-grants-2009_08
Patent number
US07576078B2

Reaction notes

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