Potassium Carbonate → (S)-2-Methyl-4-oxiranylmethoxy-1H-indole

HRID 1634719Notes

Reaction equation

[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[C:8]([OH:11])[CH:7]=[CH:6][CH:5]=2.S(C1C=CC([N+]([O-])=O)=CC=1)(O[CH2:16][C@H:17]1[O:19][CH2:18]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>>[O:19]1[CH2:18][C@H:17]1[CH2:16][O:11][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[C:2]([CH3:1])[NH:3]2

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 5902254-Hydroxy-2-methylindole

HCID 10868995(S)-(+)-Glycidyl-4-nitrobenzoate

Product 1

HCID 59032962(S)-2-Methyl-4-oxiranylmethoxy-1H-indoleYield 50.7%

Procedure

Prepared from 2-methyl-4-hydroxyindole (5 g, 33 mmol), (S)-glycidyl nosylate (8.78 g, 33 mmol) and potassium carbonate (4.56 g, 33 mmol) according to the procedure used for Intermediate 1 to give 3.4 g product as a white solid.

Sources & evidence

ORD record: ord-753d4d369ca844e7b1d07eb58be9d3b5
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06506901B2

Reaction notes

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