Water → 3-(Oxan-4-yl)azetidine

HRID 1945541Notes

Reaction equation

HRID 1945541 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH2:9]1)=O)(C)(C)C.O.C(O)(C(F)(F)F)=O>C(Cl)Cl.CO>[O:15]1[CH2:16][CH2:17][CH:12]([CH:10]2[CH2:11][NH:8][CH2:9]2)[CH2:13][CH2:14]1

Participants

6

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 59605642HCID 59605642, compound

Product 1

HCID 177856443-(Oxan-4-yl)azetidineYield 92.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(tetrahydropyran-4-yl)azetidine-1-carboxylic acid tert-butyl ester (730 mg, 3.0 mmol) in DCM (10 mL) were added water (0.15 mL) and TFA (10 mL). The reaction mixture was stirred at room temperature for 4 hours and the concentrated under reduced pressure to give a residue that was taken up in MeOH. The resulting solution was loaded onto a SCX-2 cartridge (10 g) which was washed with MeOH. The desired product was eluted with a 2M solution of ammonia in MeOH. The appropriate fractions were combined and concentrated to give 3-(Tetrahydropyran-4-yl)azetidine as a yellow oil (393 mg, 92%). 1H NMR (300 MHz, CDCl3): δ 3.96 (dd, J=11.0, 4.0, 2 H); 3.65 (dd, J=8.0, 8.0 Hz, 2 H); 3.44 (dd, J=7.6, 7.6 Hz, 2 H); 3.37 (ddd, J=11.9, 11.9, 2.1, 2 H); 2.50 (m, 1 H); 1.75 (m, 1 H); 1.53 (m, 2 H); 1.18 (ddd, J=25.0, 11.9, 4.3, 2 H).

Workup

  1. concentrationthe concentrated under reduced pressure
  2. customto give a residue that
  3. washwas washed with MeOH
  4. washThe desired product was eluted with a 2M solution of ammonia in MeOH
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7588f8f4a4894f4c898603ab5f67b93c
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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