Tetrahydrofuran → HCID 67126563, compound

HRID 1518876Notes

Reaction equation

HRID 1518876 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-989f51f4ff9841a5ac1bdfb23f40ff4c
Source dataset
uspto-grants-2015_07
Patent number
US09072748B2

Reaction notes

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