(+)-Epichlorohydrin → tert-Butyl (2S)-2-[(4-cyanophenoxy)methyl]-1-aziridinecarboxylate

HRID 411150Notes

Reaction equation

[C:1]([C:3]1[CH:20]=[CH:19][C:6]([O:7][CH2:8][CH:9]2[CH2:11][N:10]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:5][CH:4]=1)#[N:2].C([C@H]1OC1)Cl>>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][C@@H:9]2[CH2:11][N:10]2[C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])=[CH:19][CH:20]=1)#[N:2]

Participants

Reactant 2

HCID 149428(+)-Epichlorohydrin

HCID 21867670Tert-butyl 2-[(4-cyanophenoxy)methyl]-1-aziridinecarboxylate2×

Product 1

HCID 86588968tert-Butyl (2S)-2-[(4-cyanophenoxy)methyl]-1-aziridinecarboxylate

Procedure

The sub-title compound was prepared according to the procedures described in steps (i) to (v) above for the synthesis of tert-butyl 2-[(4-cyanophenoxy)methyl]-1-aziridinecarboxylate, but using (S)-(+)-epichlorohydrin in place of epichlorohydrin in step (i).

Sources & evidence

ORD record: ord-0d6a5bdd028341b2b07099d29edb1802
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06559143B1

Reaction notes

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