Hydrochloric Acid → HCID 67981150, compound

HRID 1520025Notes

Reaction equation

HRID 1520025 reaction equation
[ClH:1].C(OC([N:9]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[N:15]2)[CH2:10]1)=O)(C)(C)C>O1CCOCC1>[ClH:1].[N+:19]([C:17]1[CH:16]=[N:15][N:14]([CH:11]2[CH2:12][CH2:13][NH:9][CH2:10]2)[CH:18]=1)([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 56777240tert-butyl 3-(4-nitro-1H-pyrazol-1-yl)pyrrolidine-1-carboxylate

Product 1

HCID 67981150HCID 67981150, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of HCl (4N in dioxane, 50 mL, 150 mmol, 3.4 eq.) was added to a solution of tert-butyl-3-(4-nitro-1H-pyrazol-1-yl)pyrrolidine-1-carboxylate (prepared as described in Tetrahedron Lett. (2008), 49(18), 2996-2998, 13 g, 46 mmol, 1 eq.) in dry dioxane (75 mL) at 000° C. The reaction mixture was then stirred at RT for 5 h. It was concentrated under reduced pressure to give the title compound as an off-white solid (9.5 g, 95%). 1H NMR (400 MHz, DMSO-d6) δ 9.73 (brs, 1H), 9.46 (brs, 1H), 9.07 (s, 1H), 8.37 (s, 1H), 5.24 (m, 1H), 3.50-3.72 (m, 3H), 2.28-2.49 (m, 3H).

Workup

  1. concentrationIt was concentrated under reduced pressure

Sources & evidence

ORD record
ord-10000ee1d119442b8b49b1871029f754
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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