1,2,3,4-Tetrahydroisoquinoline → 2-(3-Phenylisoxazol-5-yl)methyl-1,2,3,4-tetrahydroisoquinoline

HRID 1978909Notes

Reaction equation

HRID 1978909 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.Br[CH2:12][C:13]1[O:17][N:16]=[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=1>CCOC(C)=O.CCCCCC>[C:18]1([C:15]2[CH:14]=[C:13]([CH2:12][N:2]3[CH2:3][CH2:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH2:1]3)[O:17][N:16]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 27487965-(Bromomethyl)-3-phenylisoxazole

Product 1

HCID 175310732-(3-Phenylisoxazol-5-yl)methyl-1,2,3,4-tetrahydroisoquinolineYield 81%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Prepared from 1,2,3,4-tetrahydroisoquinoline and 5-(bromomethyl)-3-phenylisoxazole under typical conditions. Purification by flash chromatography on silica gel 60, eluting with 25% EtOAc in hexane produced adduct 21A (81% yield). 1H NMR(300 MHz, CDCl3, δ): 7.83-7.80 (m, 2H), 7.48-7.40 (m, 3H), 7.16-7.11 (m, 3H), 7.08-6.99 (m, 1H), 6.57 (s, 1H), 3.91 (s, 2H), 3.76 (s, 2H), 3.00-2.80 (m, 4H). 13C NMR(300 MHz, CDCl3, δ): 170.25, 162.45, 134.04, 133.75, 129.97, 129.12, 128.92, 128.72, 126.81, 126.56, 126.36, 125.78, 101.26, 85.61, 53.20, 50.75, 29.03. MS(CI, NH3) m/e 291 (base, M+H+). HRMS(CI, NH3) m/e Calc'd for (M+H+): 291.1497. Found: 291.1512.

Workup

  1. customPurification by flash chromatography on silica gel 60

Sources & evidence

ORD record
ord-49578c08f8a046c989f85902c1d0d56f
Source dataset
uspto-grants-2001_05
Patent number
US06239143B1

Reaction notes

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