Sodium Carbonate → tert-Butyl 1H-pyrrol-1-ylcarbamate

HRID 1615458Notes

Reaction equation

HRID 1615458 reaction equation
CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)O1.[C:10]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])[NH:11][NH2:12].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.Cl>[N:12]1([NH:11][C:10](=[O:13])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:3]=[CH:7][CH:6]=[CH:5]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 70091tert-Butyl carbazateHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 49760548tert-Butyl 1H-pyrrol-1-ylcarbamateYield 49.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

Under an atmosphere of nitrogen, a solution of 2,5-dimethoxytetrahydrofuran (400 g, 3.03 mol) and tert-butyl carbazate (364 g, 2.75 mol) in 1,4-dioxane (2.5 L) were combined in a flask. Then, aqueous hydrochloric acid solution (2N, 35.8 mL, 71.5 mmol) was added dropwise and the reaction mixture was stirred for 21 hours at 85° C. The reaction mixture was treated with saturated sodium carbonate aqueous solution (120 mL) at room temperature. The quenched mixture was filtered to give a precipitate which was dried to give the title compound as a gray solid (250 g). The organic phase of the filtrate was concentrated and the resultant precipitate was washed with diisopropyl ether (200 mL) and filtered to give the title compound as a gray solid (60 g). The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1→3:1→2:1) to obtain the title compound (47 g). A total of 357 g of the title compound having the following physical data was obtained.

Workup

  1. filtrationThe quenched mixture was filtered
  2. customto give a precipitate which
  3. customwas dried

Sources & evidence

ORD record
ord-1e7de6a48b924a21ac7f3926fba82fc7
Source dataset
uspto-grants-2014_07
Patent number
US08765754B2

Reaction notes

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