Trifluoroacetic acid → HCID 59605308, compound

HRID 1922721Notes

Reaction equation

HRID 1922721 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:18][CH:17]([CH2:19][N:20]([CH3:26])[CH:21]2[CH2:25][CH2:24][O:23][CH2:22]2)[CH2:16]1)=O)(C)(C)C>ClCCl>[NH:15]1[CH2:18][CH:17]([CH2:19][N:20]([CH3:26])[CH:21]2[CH2:25][CH2:24][O:23][CH2:22]2)[CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59606087HCID 59606087, compound

Product 1

HCID 59605308HCID 59605308, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3 mL) was added to a solution of 3-{[methyl(tetrahydrofuran-3-yl)amino]methyl}azetidine-1-carboxylic acid tert-butyl ester (257 mg, 0.95 mmol) in dichloromethane (12 mL). The resulting reaction mixture was stirred at RT for 1.5 h. The solvents were reduced in vacuo. The resulting residue was loaded onto an Isolute® SCX-2 cartridge (5 g). The cartridge was washed with DCM/MeOH, the desired product was subsequently eluted using a mixture of 2M NH3 in MeOH and DCM to afford (Azetidin-3-ylmethyl)methyl(tetrahydrofuran-3-yl)amine as colourless oil (140 mg, 86%). 1H NMR (400 MHz, CDCl3): δ 3.94 (1H, td, J=8.62, 4.35 Hz), 3.84 (1H, dd, J=8.76, 6.50 Hz), 3.76-3.65 (3H, m), 3.62 (1H, dd, J=8.76, 6.50 Hz), 3.38 (2H, t, J=7.31 Hz), 3.09-3.07 (1H, m), 2.99-2.88 (1H, m), 2.64 (1H, dd, J=12.50, 7.22 Hz), 2.53 (1H, dd, J=12.50, 7.22 Hz), 2.15 (3H, s), 2.01 (1H, dtd, J=12.34, 7.72, 3.21 Hz), 1.83 (1H, dtd, J=12.35, 8.40, 6.96 Hz)

Workup

  1. customThe resulting reaction mixture
  2. washThe cartridge was washed with DCM/MeOH
  3. washthe desired product was subsequently eluted
  4. additiona mixture of 2M NH3 in MeOH and DCM

Sources & evidence

ORD record
ord-b3d6a4c63016432dbac247280711bdea
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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