Hydrogen chloride-ethyl acetate → (trans)-3-Azido-4-fluoropyrrolidine

HRID 928192Notes

Reaction equation

HRID 928192 reaction equation
[N:1]([C@H:4]1[C@H:8]([F:9])[CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5]1)=[N+:2]=[N-:3].Cl.CCOC(C)=O>CCOC(C)=O>[N:1]([C@H:4]1[C@H:8]([F:9])[CH2:7][NH:6][CH2:5]1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 118081950trans-Tert-butyl 3-azido-4-fluoropyrrolidine-1-carboxylate

Product 1

HCID 118073556(trans)-3-Azido-4-fluoropyrrolidineYield 126.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (trans)-tert-butyl 3-azido-4-fluoropyrrolidine-1-carboxylate (25 g, 109 mmol), as prepared in step 3 of Preparation 3, in EtOAc (100 mL) was added HCl/EtOAc (50 mL) at 0-5° C. Then the mixture was stirred at rt for 4 hr. The solid was filtered and washed with petroleum ether/EtOAc (2:1, 40 mL) to give the title compound (18 g) as a gray solid, which was used directly in the next step.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with petroleum ether/EtOAc (2:1, 40 mL)

Sources & evidence

ORD record
ord-c2d5c72fecf14a468acaea2a772f3814
Source dataset
uspto-grants-2016_03
Patent number
US09290496B2

Reaction notes

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