HCID 67937983, compound → HCID 18603873, compound

HRID 364128Notes

Reaction equation

HRID 364128 reaction equation
[C:1]([NH:5][C:6]([C@H:8]1[CH2:13][N:12]([CH3:14])[C@@H:11]2[CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=3[C:10]2=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[O-]CC.[Na+]>[C:1]([NH:5][C:6]([C@H:8]1[CH2:13][N:12]([CH3:14])[C@H:11]2[CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=3[C:10]2=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 67937983HCID 67937983, compound

Product 1

HCID 18603873HCID 18603873, compound

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Procedure

A solution of 950 mg of cis-2-(N-t-butylcarbamoyl)-9-methoxy-4-methyl-2,3,4a,5-tetrahydro-4H-[1]-benzopyrano[3,4-b]pyridine in 50 ml of 0.1M ethanolic sodium ethoxide is heated at 70° for 15 minutes. After removal of the solvent in vacuo, the residue is chromatographed over 20 g silica gel with ether/hexane 1:1 as the eluent to give trans-2-(N-t-butylcarbamoyl)-9-methoxy-4-methyl-2,3,4a,5-tetrahydro-4H-[1]-benzopyrano[3,4-b]pyridine crystallized as the hydrochloride salt, m.p. 238°-240°.

Workup

  1. customAfter removal of the solvent in vacuo
  2. customthe residue is chromatographed over 20 g silica gel with ether/hexane 1:1 as the eluent

Sources & evidence

ORD record
ord-7f5bc371f4ee47c4b10ab278222cabc6
Source dataset
uspto-grants-1986_08
Patent number
US04604397

Reaction notes

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