(Octahydro-1H-pyrido[1,2-A]pyrazin-7-YL)methanol → Racemic (7R*,9aS*)-2-(6-Chlorobenzo[d]-isoxazol-3-yl)perhydro-7-(hydroxymethyl)-1H-pyrido[1,2-a]pyrazine

HRID 466586Notes

Reaction equation

HRID 466586 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:12][N:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH:6]2[CH2:5][CH2:4]1.Cl[C:14]1[C:18]2[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:17]=2[O:16][N:15]=1>>[Cl:23][C:21]1[CH:20]=[CH:19][C:18]2[C:14]([N:10]3[CH2:9][CH2:8][N:7]4[CH2:12][CH:3]([CH2:2][OH:1])[CH2:4][CH2:5][CH:6]4[CH2:11]3)=[N:15][O:16][C:17]=2[CH:22]=1

Participants

3

Reactant 2

HCID 12985539(Octahydro-1H-pyrido[1,2-A]pyrazin-7-YL)methanolHCID 135684493,6-Dichlorobenzo[d]isoxazole

Product 1

HCID 67766479Racemic (7R*,9aS*)-2-(6-Chlorobenzo[d]-isoxazol-3-yl)perhydro-7-(hydroxymethyl)-1H-pyrido[1,2-a]pyrazineYield 53.8%

Procedure

By the method of Example 4, the alcohol-amine title product of Example 3 (203 mg, 1.19 mmol) and 3,6-dichlorobenzo[d]isoxazole were converted into present title product (206 mg, 53.8% yield) isolated as a pale yellow amorphous solid. In this product the 7and 9a-hydrogen substitutents remain trans. TLC Rf (methylene chloride/methanol=9:1 in volume; potassium permanganate spray): 0.41. 13CNMR (CDCl3) delta 164.2, 160.6, 136.1, 123.3, 122.8, 114.9, 110.8, 65.9, 60.2, 58.7, 54.1, 53.4, 48.0, 39.0, 28.8, 26.7.

Sources & evidence

ORD record
ord-1b463b3ec8c14531bd59e95d3687f9d2
Source dataset
uspto-grants-1992_10
Patent number
US05157034

Reaction notes

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