3-(2-Bromoacetyl)pyridine hydrobromide → (S)-3-Oxiranyl-pyridine

HRID 1061282Notes

Reaction equation

HRID 1061282 reaction equation
B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@@H]2N1CCC2.Br.Br[CH2:24][C:25]([C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)=[O:26]>>[O:26]1[CH2:24][C@H:25]1[C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 27762343-(2-Bromoacetyl)pyridine hydrobromideHCID 9838490(R)-2-Methyl-CBS-oxazaborolidine

Product 1

HCID 13319559(S)-3-Oxiranyl-pyridine

Procedure

The title compound was prepared from (R)-2-methyl-CBS-oxazaborolidine monohydrate and 3-(2-bromoacetyl)pyridine hydrobromide in substantially the same manner, as described in Example 123. The product was obtained as an oil; 1H NMR (300 MHz, DMSO-d6) δ 2.94-2.97 (m, 1H), 3.14-3.17 (m, 1H), 3.99-4.01 (m, 1H), 7.36-7.40 (m, 1H), 7.63-7.66 (m, 1H), 8.51-8.55 (m, 2H); MS (ES) m/z: 121 (M+).

Workup

  1. customThe product was obtained as an oil

Sources & evidence

ORD record
ord-c43fc37af9f344afa0de9adffd22f519
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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