2-Pyridineethanamine → (3R-trans)-4-[(2-Pyridinylethyl)amino]-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-l-benzopyran-6-carbonitrile

HRID 356673Notes

Reaction equation

HRID 356673 reaction equation
[CH3:1][C:2]1([CH3:15])[C@@H:7]2[O:8][C@@H:6]2[C:5]2[CH:9]=[C:10]([C:13]#[N:14])[CH:11]=[CH:12][C:4]=2[O:3]1.[C:16]([C:18]1[CH:19]=[CH:20][C:21]2OC(C)(C)[C@H](O)[C@@H:23]([N:30](CC(OCC)=O)C3C=CC=CC=3)[C:22]=2C=1)#[N:17].NCCC1C=CC=CN=1>>[N:17]1[CH:16]=[CH:18][CH:19]=[CH:20][C:21]=1[CH2:22][CH2:23][NH:30][C@H:6]1[C:5]2[CH:9]=[C:10]([C:13]#[N:14])[CH:11]=[CH:12][C:4]=2[O:3][C:2]([CH3:15])([CH3:1])[C@@H:7]1[OH:8]

Participants

4

Reactant 3

HCID 759192-PyridineethanamineHCID 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 18666859(3R-trans)-4-[(2-Pyridinylethyl)amino]-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-l-benzopyran-6-carbonitrile

Procedure

A solution of (1aR-cis)-1a,7b-dihydro-2,2-dimethyl-2H-oxireno-[c][1]benzopyran-6-carbonitrile ((1.0 g, 5.0 mmol, the title A compound of Example 3) and 2-aminoethylpyridine (1.1 g, 9.0 mmol) was heated in a sealed tube at 75° C. for 18 hours. The reaction mixture was cooled to room temperature and purified by flash chromatography to afford an oil, which solidified upon standing (1.4 g, 87%).

Workup

  1. custompurified by flash chromatography
  2. customto afford an oil, which

Sources & evidence

ORD record
ord-d9b01e64f56743439636f3b46afb8142
Source dataset
uspto-grants-1998_11
Patent number
US05837702

Reaction notes

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