Sodium hydride → [1-(2-Cyanofuran-4-ylmethyl)-2-oxopyrrolidin-3-yl]carbamic acid tert-butyl ester

HRID 619869Notes

Reaction equation

HRID 619869 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:13])([CH3:4])([CH3:3])[CH3:2].Br[CH2:16][C:17]1[CH:21]=[C:20]([C:22]#[N:23])[O:19][CH:18]=1.[H-].[Na+].CO.C(Cl)Cl>C1COCC1.CN(C=O)C>[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:12][CH2:11][N:10]([CH2:16][C:17]2[CH:21]=[C:20]([C:22]#[N:23])[O:19][CH:18]=2)[C:9]1=[O:13])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 106551253-Bromomethylfuran-5-carbonitrileHCID 10750535(S)-tert-Butyl (2-oxopyrrolidin-3-yl)carbamateHCID 21226129Dichloromethane methanol

Product 1

HCID 54441437[1-(2-Cyanofuran-4-ylmethyl)-2-oxopyrrolidin-3-yl]carbamic acid tert-butyl esterYield 200%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

A solution of (2-oxopyrrolidin-3-(S)-yl)carbamic acid tert-butyl ester (0.78 g, 3.9 mmol) in 40 mL of THF:DMF (5:1) is treated with 3-bromomethylfuran-5-carbonitrile (0.78 g, 3.9 mmol) and sodium hydride (60%) (0.10 g, 4.2 mmol) as described in EXAMPLE 122, Part F. After addition, the solution is allowed to warm to ambient temperatures. Standard workup folowed by chromatography (5-10% MeOH/CH2Cl2) affords [1-(2-cyanofuran-4-ylmethyl)-2-oxopyrrolidin-3-yl]carbamic acid tert-butyl ester (1.05 g, 7.8 mmol) as a white solid. This material is treated with trimethylsilyliodide (0.844 g, 4.22 mmol) and free based with Amberlite (OH) resin to yield the title compound (0.926 g, 4.51 mmol).

Workup

  1. additionAfter addition
  2. temperatureto warm to ambient temperatures

Sources & evidence

ORD record
ord-f9bf36f5220148418d417655d2e96001
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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