Tert-butyl 3-oxopyrrolidine-1-carboxylate → HCID 23112167, compound

HRID 1373063Notes

Reaction equation

HRID 1373063 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([CH:12]=[CH2:13])=[CH:5][N:6]=[CH:7]2.O=[C:15]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16]1.[BH4-].[Na+].C(=O)([O-])O.[Na+]>ClCCl.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].C(OCC)(=O)C.CO>[CH:12]([C:4]1[C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[NH:1][CH:19]2[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18]2)[CH:7]=[N:6][CH:5]=1)=[CH2:13]

Participants

9

Reactant 4

HCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 23112198HCID 23112198, compound

Product 1

HCID 23112167HCID 23112167, compoundYield 64.1%

Reagents, catalysts & solvents 4

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Intermediate 1 (251 mg), and tert-butyl 3-oxo-1-pyrrolidinecarboxylate (563 mg, AstaTech) in dichloromethane (85 ml) was added with titanium tetraisopropoxide (905 μl, Aldrich) at room temperature, and stirred at room temperature for 19 hours. The reaction mixture was added with methanol (6 ml), and sodium borohydride (249 mg, Kanto Chemicals), and stirred at room temperature for 3.5 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate (20 ml), and ethyl acetate (20 ml), and then the precipitates were removed by filtration. Then, the organic layer was separated, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to obtain the title compound (321 mg).

Workup

  1. stirringstirred at room temperature for 3.5 hours
  2. customthe precipitates were removed by filtration
  3. customThen, the organic layer was separated
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-42ab8eda748e4e33a74fccb124bb2a84
Source dataset
uspto-grants-2007_01
Patent number
US07160894B2

Reaction notes

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