Ethyl Acetate → HCID 67246961, compound

HRID 1430559Notes

Reaction equation

HRID 1430559 reaction equation
[CH3:1][CH2:2][N:3]([CH:7]([CH3:9])C)[CH:4]([CH3:6])C.N1CCCC1.BrC[C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=C[C:18]=1[F:26].CCOC(C)=O>C1COCC1>[F:26][C:18]1[CH:17]=[CH:22][C:21]([N+:23]([O-:25])=[O:24])=[CH:20][C:9]=1[CH2:7][N:3]1[CH2:2][CH2:1][CH2:6][CH2:4]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 103539672-(Bromomethyl)-1-fluoro-4-nitrobenzene

Product 1

HCID 67246961HCID 67246961, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A −20° C. mixture of DIEA (552 mg, 4.27 mmol) and pyrrolidine (152 mg, 2.137 mmol) in THF (5 mL) was treated drop-wise with a solution of 2-(bromomethyl)-1-fluoro-4-nitrobenzene (500 mg, 2.137 mmol) in THF (5 mL), allowed to warm to RT and stirred for 6 h. The mixture was treated with EtOAc, washed with water, then brine, dried over Na2SO4 and concentrated to dryness to afford 1-(2-fluoro-5-nitrobenzyl)pyrrolidine (450 mg, 94% yield). MS (ESI) m/z: 225.1 [M+H]+.

Workup

  1. washwashed with water
  2. dry with materialbrine, dried over Na2SO4
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-b43aa1da6bda41f192e25fdd0044b395
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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