Diisopropylethylamine → HCID 59239835, compound

HRID 1668372Notes

Reaction equation

HRID 1668372 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16]Br)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.Cl.[F:29][C@H:30]1[CH2:34][CH2:33][NH:32][CH2:31]1>CN(C=O)C.CO.C(OCC)(=O)C.CCCCCC>[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:32]2[CH2:33][CH2:34][C@H:30]([F:29])[CH2:31]2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 3

HCID 81531DiisopropylethylamineHCID 16217739(s)-3-Fluoropyrrolidine hydrochlorideHCID 59239819[2-(4-(broMoMethyl)phenyl)ethyl]carbaMic acid tert-butyl ester

Product 1

HCID 59239835HCID 59239835, compoundYield 79%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent3×

Procedure

To a solution of tert-butyl{2-[4-(bromomethyl)phenyl]ethyl}carbamate (450 mg, 1.43 mmol) in DMF (4 ml) were added N,N-diisopropylethylamine (0.749 ml, 4.30 mmol) and (3S)-3-fluoropyrrolidine hydrochloride (180 mg, 1.43 mmol), and the mixture was stirred at room temperature for 22 hr. Ethyl acetate was added to the reaction mixture, and the mixture was washed with aqueous sodium hydrogen carbonate solution and brine. The solvent was evaporated under reduced pressure, and the residue was purified by NH-silica gel chromatography (developing solvent; ethyl acetate), and then silica gel chromatography (developing solvent; hexane:ethyl acetate=1:1 (volume ratio)→ethyl acetate:methanol=9:1 (volume ratio)) to give the title compound (364 mg, 1.13 mmol) as a colorless liquid.

Workup

  1. washthe mixture was washed with aqueous sodium hydrogen carbonate solution and brine
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by NH-silica gel chromatography (developing solvent; ethyl acetate)

Sources & evidence

ORD record
ord-91e09565e6024347b62469c9dfb7b5c4
Source dataset
uspto-grants-2011_08
Patent number
US07989445B2

Reaction notes

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