Sodium Hydroxide → (1aS,7bS)-2,2-Dimethyl-1a,7b-dihydro-2H-oxireno[2,3-c]chromene-6-carbonitrile

HRID 704776Notes

Reaction equation

HRID 704776 reaction equation
[OH-].[Na+].C(OC(N[C@@H](C)C([O:17][C@H:18]1[C:23]2[CH:24]=[C:25]([C:28]#[N:29])[CH:26]=[CH:27][C:22]=2[O:21][C:20]([CH3:31])([CH3:30])[C@@H:19]1Br)=O)=O)C1C=CC=CC=1>O.O1CCOCC1>[O:17]1[C@@H:18]2[C@H:19]1[C:20]([CH3:30])([CH3:31])[O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][C:23]=12

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18643511(3R,4S)-4-{(2S)-2-benzyloxycarbonylaminopropionyloxy}-3-bromo-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

Product 1

HCID 9837089(1aS,7bS)-2,2-Dimethyl-1a,7b-dihydro-2H-oxireno[2,3-c]chromene-6-carbonitrileYield 87.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of sodium hydroxide (0.672 g) in water (16 ml) was added dropwise to a stirred solution of (3R,4S)-4-{(2S)-2-benzyloxycarbonylaminopropionyloxy}-3-bromo-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (3.896 g) in 1,4-dioxane (24 ml). After being stirred at ambient temperature for 1 hour, the mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The crystalline residue was washed with isopropyl ether and dried to give (3S,4S)-3,4-epoxy-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (1.401 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. washThe crystalline residue was washed with isopropyl ether
  6. customdried

Sources & evidence

ORD record
ord-602ec3827b6642d982cfd269fadfc365
Source dataset
uspto-grants-1991_01
Patent number
US04988723

Reaction notes

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