Tetrahydrofuran → HCID 18785874, compound

HRID 1107731Notes

Reaction equation

HRID 1107731 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[ClH:19].[NH2:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][CH:23]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2O[Si](C(C)(C)C)(C)C)[N:22]=1.C1C[O:48]CC1>>[ClH:19].[NH2:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][CH:23]([C:31]2[CH:36]=[CH:35][C:34]([OH:48])=[CH:33][CH:32]=2)[N:22]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 18785969HCID 18785969, compound

Product 1

HCID 18785874HCID 18785874, compound

Procedure

Tetra-n-butylammonium fluoride (1.0M in THF, 3.3 ml) was added to a stirred solution of 1-amino-3-(tert-butyldimethylsilyloxyphenyl)-3,4-dihydroisoquinoline hydrochloride (638 mg, 1.11 mmol) in THF (10 ml). After 15 min., the mixture was evaporated and the residue purified by flash chromatography on untreated neutral alumina, eluting with 5% methanol in dichloromethane, increasing the gradient to 40% methanol in dichloromethane to give a colourless solid (172 mg). This was recrystallised from methanol/dichloromethane (1:2) to give the product as a white powder. M+ 239; 360 MHz 1H n.m.r (d6 -DMSO) 9.65 (1H, br.s), 8.15 (1H, d, J 7.8 Hz), 7.69 (1H, t, J 7.5 Hz), 7.52 (1H, t, J 7.6 Hz), 7.45 (1H, d, J 7.5 Hz), 7.19 (2H, d, J 8.6 Hz), 6.77 (2H, d, J 8.6 Hz), 4.87 (1H, t, J 7.3 Hz), 3.25 (2H, d, J 7.3 Hz).

Workup

  1. customthe mixture was evaporated
  2. customthe residue purified by flash chromatography on untreated neutral alumina
  3. washeluting with 5% methanol in dichloromethane
  4. temperatureincreasing the gradient to 40% methanol in dichloromethane

Sources & evidence

ORD record
ord-7e329737febf4ef5995b577b3aada5a2
Source dataset
uspto-grants-2000_05
Patent number
US06063789

Reaction notes

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