Tetrahydrofuran → HCID 67126563, compound

HRID 2045077Notes

Reaction equation

HRID 2045077 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.O1CCCC1.C(N(C(C)C)C(C)C)C.F[C:29]1[CH:34]=[CH:33][C:32]([S:35]([NH2:38])(=[O:37])=[O:36])=[CH:31][C:30]=1[N+:39]([O-:41])=[O:40]>CN(C)C=O>[N+:39]([C:30]1[CH:31]=[C:32]([S:35](=[O:37])(=[O:36])[NH2:38])[CH:33]=[CH:34][C:29]=1[NH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1)([O-:41])=[O:40]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 854070(R)-(+)-1-Boc-3-aminopyrrolidineHCID 167824874-Fluoro-3-nitrobenzenesulfonamide

Product 1

HCID 67126563HCID 67126563, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (R)-tert-butyl 3-aminopyrrolidine-1-carboxylate (1.0 g), tetrahydrofuran (50 ml), N-ethyl-N-isopropylpropan-2-amine (5.61 mL) and N,N-dimethylformamide (10 mL) was added 4-fluoro-3-nitrobenzenesulfonamide (1.212 g) and the mixture was stirred for 18 hours. The crude product was isolated by concentration and was the material was purified on silica gel, and was eluted with a 30, 50, and 75% ethyl acetate in hexane step gradient to provide the title compound.

Workup

  1. customThe crude product was isolated by concentration
  2. customwas purified on silica gel
  3. washwas eluted with a 30, 50, and 75% ethyl acetate in hexane step gradient

Sources & evidence

ORD record
ord-6119ebd4390b4cd580243d4d17ae4a85
Source dataset
uspto-grants-2013_11
Patent number
US08586754B2

Reaction notes

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