Tetrahydrofuran → HCID 67126563, compound

HRID 629655Notes

Reaction equation

HRID 629655 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-324e9bf62a2e49e58342b6a6edff7391
Source dataset
uspto-grants-2016_04
Patent number
US09315488B2

Reaction notes

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