Sodium hydride → Tert-butyl 4-cyano-2,2-dimethyl-3-oxopyrrolidine-1-carboxylate

HRID 1479040Notes

Reaction equation

HRID 1479040 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]([CH2:18][CH2:19][C:20]#[N:21])[C:11]([CH3:17])([CH3:16])[C:12]([O:14]C)=O)=[O:9])([CH3:6])([CH3:5])[CH3:4]>O1CCOCC1>[C:20]([CH:19]1[CH2:18][N:10]([C:8]([O:7][C:3]([CH3:4])([CH3:5])[CH3:6])=[O:9])[C:11]([CH3:17])([CH3:16])[C:12]1=[O:14])#[N:21]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 57523645methyl N-(tert-butoxycarbonyl)-N-(2-cyanoethyl)-2-methylalaninate

Product 1

HCID 42609241Tert-butyl 4-cyano-2,2-dimethyl-3-oxopyrrolidine-1-carboxylateYield 79.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

NaH (60%, 3 g; 73.2 mmol) was added to a solution of methyl 2-[(tert-butoxycarbonyl)(2-cyanoethyl)amino]-2-methylpropanoate (16.5 g, 61.0 mmol) in 1,4-dioxane (300 mL) and the reaction mixture was stirred at 100° C. for 4 hours then concentrated in vacuo. The residue was taken up in water (200 mL) and the pH adjusted to 3.5 with citric acid. The solution was extracted with EA (2×). The combined organics were washed with brine, dried over magnesium sulfate and concentrated in vacuo to afford the title compound (11.5 g, 79%) as an off-white solid. 1H NMR (DMSO-d6) δ 12.24 (s, 1H), 4.02-3.98 (m, 2H), 1.46-1.39 (m, 15H).

Workup

  1. concentrationthen concentrated in vacuo
  2. extractionThe solution was extracted with EA (2×)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-68eba5224f284f08900030e795b56255
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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