3-Methylbutanal → HCID 18441751, compound

HRID 458147Notes

Reaction equation

HRID 458147 reaction equation
[CH2:1]([N:8]1[CH2:18][CH2:17][C:11]2([NH:15][CH2:14][NH:13][C:12]2=[O:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:19](=O)[CH2:20][CH:21]([CH3:23])[CH3:22].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]2([N:15]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:14][NH:13][C:12]2=[O:16])[CH2:17][CH2:18]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 115523-MethylbutanalHCID 5049666Sodium triacetoxyborohydrideHCID 105383388-benzyl-1,3,8-triazaspiro[4.5]decan-4-one

Product 1

HCID 18441751HCID 18441751, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 100 mg (0.408 mmol) 8-benzyl-1,3,8-triaza-spiro[4,5]decan-4-one (m.p. 164–166° C.) and 0.062 ml (49.2 mg, 0.571 mmol) isovaleraldehyde in 3 ml 1,2-dichloroethane were added 130 mg (0.611 mmol) sodium triacetoxyborohydride and the mixture stirred at ambient temperature for 16 h. Then the reaction mixture was quenched with 10 ml saturated aqueous NaHCO3-solution and extracted with dichloromethane. The organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated: 128 mg 8-benzyl-1-(3-methyl-butyl)-1,3,8-triaza-spiro[4.5]decan-4-one as colorless crystals: m.p. 139–140° C., MS (ISP): 316.4 MH+.

Workup

  1. customThen the reaction mixture was quenched with 10 ml saturated aqueous NaHCO3-solution
  2. extractionextracted with dichloromethane
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-1a26af7f9bbd4c739739dc46a7a50279
Source dataset
uspto-grants-2007_03
Patent number
US07189850B2

Reaction notes

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