Tetrabutylammonium Fluoride → HCID 58779114, compound

HRID 1666856Notes

Reaction equation

HRID 1666856 reaction equation
[CH2:1]([O:4][C:5]1[CH:16]=[C:15]2[C:8]([N:9]([Si](C(C)C)(C(C)C)C(C)C)[CH:10]=[C:11]2[CH2:12][CH2:13][NH2:14])=[CH:7][CH:6]=1)[CH2:2][CH3:3].[F:27][C:28]([F:42])([CH:39]([F:41])[F:40])[CH2:29][O:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=1)[CH:34]=O.[BH4-].[Na+].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CCO.C(Cl)(Cl)Cl.CO>[CH2:1]([O:4][C:5]1[CH:16]=[C:15]2[C:8](=[CH:7][CH:6]=1)[NH:9][CH:10]=[C:11]2[CH2:12][CH2:13][NH:14][CH2:34][C:33]1[CH:36]=[CH:37][CH:38]=[C:31]([O:30][CH2:29][C:28]([F:27])([F:42])[CH:39]([F:40])[F:41])[CH:32]=1)[CH2:2][CH3:3]

Participants

8

Reactant 4

HCID 2724141Tetrabutylammonium FluorideHCID 4311764Sodium borohydrideHCID 21071449HCID 21071449, compoundHCID 21071593HCID 21071593, compound

Product 1

HCID 58779114HCID 58779114, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

Combine 2-(5-propoxy-1-triisopropylsilanyltryptamine (138 mg, 0.37 mmol), 3-(2,2,3,3-tetrafluoropropoxy)benzaldehyde (87 mg, 1.8 mmol) and 1 g 3 Å molecular sieves in 25 mL EtOH and reflux overnight. Decant the liquid into a separate flask, cool to 0° C. and treat with 42 mg (1.1 mmol) NaBH4. Stir the reaction at ambient temperature for 1 hour, treat with 0.74 mmol of tetrabutylammonium fluoride and stir for an additional hour. Concentrate under vacuum to give a residue. Chromatograph the residue on silica gel eluting with 10% MeOH in CHCl3 to give the title compound. Treat the title compound with 10 mL EtOH with 0.25 mL 5 N HCl and 40 mL toluene then concentrating gives the hydrochloride of the title compound: ISMS 439 (M+1); 1H NMR (Free base-CDCl3) 7.89 (bs, 1H), 7.23-7.21 (m, 1H), 7.03-7.02 (d, 1H), 6.99-6.98 (d, 1H), 6.94-6.92 (m, 1H), 6.89-6.83 (m, 2H), 6.78-6.75 (m, 1H), 6.18-5.90 (m, 1H), 4.29-4.23 (m, 2H), 3.95-3.91 (m, 2H), 3.78 (s, 2H), 2.95 (s, 4H), 1.85-1.75 (m, 2H), 1.51 (bs, 1H), 1.06-1.03 (t, 3H).

Workup

  1. customDecant the liquid into a separate flask
  2. customthe reaction at ambient temperature for 1 hour
  3. stirringstir for an additional hour
  4. concentrationConcentrate under vacuum
  5. customto give a residue

Sources & evidence

ORD record
ord-f1d7165192cb49c2ae8f68c8763d097a
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

Loading…