Acetone → HCID 86588810, compound

HRID 1583056Notes

Reaction equation

HRID 1583056 reaction equation
[CH:1](N(C(C)C)CC)([CH3:3])[CH3:2].CC(C)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH3:28][C:29]1[CH:38]=[C:37]([CH2:39][C:40]2[CH:57]=[CH:56][C:43]([C:44]([NH:46][C@@H:47]3[CH2:51][NH:50][CH2:49][C@@H:48]3[C:52]([O:54][CH3:55])=[O:53])=[O:45])=[CH:42][CH:41]=2)[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:30]=1>ClCCl.C(OCC)(=O)C>[CH:1]([N:50]1[CH2:51][C@@H:47]([NH:46][C:44](=[O:45])[C:43]2[CH:42]=[CH:41][C:40]([CH2:39][C:37]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=[C:29]([CH3:28])[CH:38]=3)=[CH:57][CH:56]=2)[C@@H:48]([C:52]([O:54][CH3:55])=[O:53])[CH2:49]1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 180AcetoneHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86588809HCID 86588809, compound

Product 1

HCID 86588810HCID 86588810, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diisopropylethylamine (28 mg, 38 μL, 0.22 mmol), acetone (6 mg, 8 μL) and NaBH(OAc)3 (23 mg, 0.11 mmol) were added to a solution of the TFA salt (403a) (46 mg, 0.073 mmol) in 1 mL of dichloromethane. 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-isopropyl-4-({4-[(2-methyl-4-quinolinyl)methyl]benzoyl}amino)-3-pyrrolidinecarboxylate (20 mg, 63%). MS (ES+): 446(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-5aa0b35eaf7a4dc087f3462b67102381
Source dataset
uspto-grants-2004_05
Patent number
US06740649B2

Reaction notes

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