Ammonium Hydroxide → (3R,4S)-4-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

HRID 356671Notes

Reaction equation

HRID 356671 reaction equation
CC1(C)[C@@H]2O[C@@H]2C2C=C(C#N)C=CC=2O1.[C:16]([C:18]1[CH:19]=[CH:20][C:21]2[O:26][C:25]([CH3:28])([CH3:27])[C@H:24]([OH:29])[C@@H:23]([N:30](CC(OCC)=O)C3C=CC=CC=3)[C:22]=2[CH:43]=1)#[N:17].[OH-].[NH4+]>O1CCCC1>[NH2:30][C@H:23]1[C:22]2[CH:43]=[C:18]([C:16]#[N:17])[CH:19]=[CH:20][C:21]=2[O:26][C:25]([CH3:27])([CH3:28])[C@@H:24]1[OH:29]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 10738551(3R-trans)-[(6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl)phenylamino]acetic acid, ethyl esterHCID 10987295(1aR,7bR)-2,2-Dimethyl-1a,7b-dihydro-2H-oxireno[2,3-c]chromene-6-carbonitrile

Product 1

HCID 14511095(3R,4S)-4-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of (1aR-cis)-1a,7b-dihydro-2,2-dimethyl-2H-oxireno-[c][1]benzopyran-6-carbonitrile ((2.5 g, 12.4 mmol, the title A compound of Example 3) in tetrahydrofuran in a re-sealable tube was added concentrated ammonium hydroxide (2 mL). The tube was sealed and the solution was heated on an oil bath at 75° C. overnight. The resultant solution was cooled to room temperature, concentrated and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated to yield the title compound as an oil.

Workup

  1. customThe tube was sealed
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-558d8f8c500d4b7eb41d5e99e9e242da
Source dataset
uspto-grants-1998_11
Patent number
US05837702

Reaction notes

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