(3R-trans)-[(6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl)phenylamino]acetic acid, ethyl ester → (3R-trans)-3,4-Dihydro-4-[(2,2-dimethoxyethyl)amino]-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

HRID 356665Notes

Reaction equation

HRID 356665 reaction equation
[CH3:1]C1(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]([CH2:37][C:38]([O:40][CH2:41]C)=[O:39])C3C=CC=CC=3)[C:22]=2[CH:43]=1)#[N:17]>>[CH3:41][O:40][CH:38]([O:39][CH3:1])[CH2:37][NH: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

3

Reactant 2

HCID 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 67641785(3R-trans)-3,4-Dihydro-4-[(2,2-dimethoxyethyl)amino]-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrileYield 90%

Procedure

A mixture of (1aR-cis)-1a,7b-dihydro-2,2-dimethyl-2H-oxireno-[c][1]benzopyran-6-carbonitrile (750 mg, 3.73 mmol, the title A compound of Example 3), dimethyl aminoacetal (1.2 mL) was heated in a sealed tube at 75° C. for two days. The reaction mixture was purified by flash column chromatography (ethyl acetate and hexane, 1:1) to give a colorless oil (1.0 g, 90%).

Workup

  1. customThe reaction mixture was purified by flash column chromatography (ethyl acetate and hexane, 1:1)

Sources & evidence

ORD record
ord-c9e762e53535407c8ead3a24e10d02f5
Source dataset
uspto-grants-1998_11
Patent number
US05837702

Reaction notes

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