Dimethylformamide → HCID 131736489, compound

HRID 1477607Notes

Reaction equation

HRID 1477607 reaction equation
CN(C)C=O.[CH2:6]([NH:13][C@H:14]1[C@H:18]([OH:19])[CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.O>[CH2:6]([N:13]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C@H:14]1[C@H:18]([OH:19])[CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 25219891tert-Butyl (3R,4R)-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 131736489HCID 131736489, compoundYield 107.3%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an N,N-dimethylformamide solution (2.5 mL) of tert-butyl (3R,4R)-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate (500 mg, 1.70 mmol), benzyl bromide (203 μL, 1.70 mmol) was added at room temperature and the resultant solution was stirred for 1 day. To the reaction solution, tetrabutylammonium iodide (188 mg, 0.51 mmol) and potassium carbonate (470 mg, 3.40 mmol) were added and the resultant mixture was stirred for 1 day. After completion of the reaction, water was added to the reaction solution and extraction with ethyl acetate from the resultant mixture was performed. The organic layer was washed with brine and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0→1/1 (v/v)) to obtain the title compound (698 mg, quantitative).

Workup

  1. washThe organic layer was washed with brine
  2. concentrationconcentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0→1/1 (v/v))

Sources & evidence

ORD record
ord-4de4fa991246485b9ea1b8fb5f8b77de
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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