Sodium Bicarbonate → HCID 22293590, compound

HRID 966985Notes

Reaction equation

HRID 966985 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:15]1([C:21]2([CH:31]=O)[CH2:30][CH2:29][C:24]3([O:28][CH2:27][CH2:26][O:25]3)[CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[F:33][C:34]([F:48])([F:47])[C:35]1[CH:36]=[C:37]([CH2:45][NH2:46])[CH:38]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:40]=1.C(=O)([O-])O.[Na+]>ClC(Cl)C>[C:15]1([C:21]2([CH2:31][NH:46][CH2:45][C:37]3[CH:38]=[C:39]([C:41]([F:42])([F:43])[F:44])[CH:40]=[C:35]([C:34]([F:33])([F:47])[F:48])[CH:36]=3)[CH2:30][CH2:29][C:24]3([O:25][CH2:26][CH2:27][O:28]3)[CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 122302758-phenyl-1,4-dioxaspiro[4,5]decane-8-carboxaldehyde

Product 1

HCID 22293590HCID 22293590, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (4.77 g, 22.5 mmol) was added to a solution of 8-phenyl-1,4-dioxaspiro[4.5]decane-8-carboxaldehyde (J. Med. Chem. 1975, 18, 593-599). (1.1 g, 4.5 mmol) and 3,5-bis(trifluoromethyl)benzenemethanamine (1.1 g, 4.5 mmol) in dichloroethane (50 mL) and the mixture was stirred at room temperature overnight. The mixture was poured into saturated aqueous sodium hydrogen carbonate (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic fractions were washed with brine (50 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (75:25), to give the title compound as a yellow oil (1.0 g, 47%). m/z (ES+) 473 (M+1).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washThe combined organic fractions were washed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with isohexane/EtOAc (75:25)

Sources & evidence

ORD record
ord-b445ca2be2d340d897eec9d678f27034
Source dataset
uspto-grants-2005_10
Patent number
US06953792B2

Reaction notes

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