Isobutyraldehyde → HCID 86588811, compound

HRID 1583057Notes

Reaction equation

HRID 1583057 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH2:12][C:13]2[CH:30]=[CH:29][C:16]([C:17]([NH:19][C@@H:20]3[CH2:24][NH:23][CH2:22][C@@H:21]3[C:25]([O:27][CH3:28])=[O:26])=[O:18])=[CH:15][CH:14]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(C(C)C)CC)(C)C.[CH:40](=O)[CH:41]([CH3:43])[CH3:42].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl.C(OCC)(=O)C>[CH2:40]([N:23]1[CH2:24][C@@H:20]([NH:19][C:17](=[O:18])[C:16]2[CH:15]=[CH:14][C:13]([CH2:12][C:10]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=[C:2]([CH3:1])[CH:11]=3)=[CH:30][CH:29]=2)[C@@H:21]([C:25]([O:27][CH3:28])=[O:26])[CH2:22]1)[CH:41]([CH3:43])[CH3:42]

Participants

7

Reactant 4

HCID 6561IsobutyraldehydeHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86588809HCID 86588809, compound

Product 1

HCID 86588811HCID 86588811, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The TFA salt (403a) (70 mg, 0.11 mmol) was dissolved in 1 mL of dichloromethane. Diisopropylethylamine (43 mg, 60 μL, 0.33 mmol), isobutyraldehyde (12 mg, 5 μL) and NaBH(OAc)3 (35 mg, 0.17 mmol) were added. The whole mixture was stirred until the reaction went to completion. The solution was diluted with ethyl acetate and washed with saturated NaHCO3, H2O and brine. The organic layer was dried over MgSO4. After filtration and concentration, the residue was purified on silica gel to provide methyl (3S,4S)-1-isobutyl-4-({4-[(2-methyl-4-quinolinyl)methyl]benzoyl}amino)-3-pyrrolidinecarboxylate (40 mg, 78%). MS (ES+): 460 (M+1).

Workup

  1. washwashed with saturated NaHCO3, H2O and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationAfter filtration and concentration
  4. customthe residue was purified on silica gel

Sources & evidence

ORD record
ord-941ccf524c514f12bd92050afb2e32af
Source dataset
uspto-grants-2004_05
Patent number
US06740649B2

Reaction notes

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