Tert-butyl 3-(3-fluoroazetidin-1-yl)azetidine-1-carboxylate → 3-Fluoro-1,3′-biazetidine

HRID 1922667Notes

Reaction equation

HRID 1922667 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([N:12]2[CH2:15][CH:14]([F:16])[CH2:13]2)[CH2:9]1)=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[F:16][CH:14]1[CH2:15][N:12]([CH:10]2[CH2:11][NH:8][CH2:9]2)[CH2:13]1

Participants

3

Reactant 1

HCID 59605557Tert-butyl 3-(3-fluoroazetidin-1-yl)azetidine-1-carboxylate

Product 1

HCID 596057843-Fluoro-1,3′-biazetidineYield 94.8%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A 25 mL round-bottomed flask was charged with a solution of 3-fluoro-[1,3′]biazetidinyl-1′-carboxylic acid tert-butyl ester (0.109 g, 0.47 mmol) in DCM/TFA (2 mL/2 mL). The reaction mixture was stirred for 90 min at room temperature. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the desired product was eluted using 2 M NH3 in MeOH to give 3-Fluoro-[1,3′]biazetidinyl as a colourless oil (0.058 g, 94%). 1H NMR (CDCl3, 400 MHz) δ 5.14 (dp, J=57.2, 5.3 Hz, 1H); 3.75-3.46 (m, 8H); 3.34-3.24 (m, 1H); 3.27-3.10 (m, 1H).

Workup

  1. washThe cartridge was washed with MeOH
  2. washthe desired product was eluted

Sources & evidence

ORD record
ord-181c99dd77f54696b5dc56725e258693
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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