Ammonium Hydroxide → (3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

HRID 543468Notes

Reaction equation

HRID 543468 reaction equation
[C:1]([C:3]1[CH:15]=[CH:14][C:6]2[O:7][C:8]([CH3:13])([CH3:12])[CH:9]3[O:11][CH:10]3[C:5]=2[CH:4]=1)#[N:2].[OH-].[NH4+:17]>>[C:1]([C:3]1[CH:15]=[CH:14][C:6]2[O:7][C:8]([CH3:13])([CH3:12])[C@@H:9]([OH:11])[C@H:10]([NH2:17])[C:5]=2[CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochroman

Product 1

HCID 10943936(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

Procedure

The title compound was prepared by stirring 6-cyano-3,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-benzo[b]pyran in ethanolic ammonium hydroxide solution at room temperature until thin layer chromatography showed consumption of the starting epoxide.

Workup

  1. customconsumption of the starting epoxide

Sources & evidence

ORD record
ord-0c51afcb8e85487a8e366d4ef48a295b
Source dataset
uspto-grants-1984_05
Patent number
US04446113

Reaction notes

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