Trifluoroacetic acid → HCID 59606118, compound

HRID 1922719Notes

Reaction equation

HRID 1922719 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:18][CH:17]([CH:19]([OH:23])[CH:20]([CH3:22])[CH3:21])[CH2:16]1)=O)(C)(C)C>ClCCl>[NH:15]1[CH2:18][CH:17]([CH:19]([OH:23])[CH:20]([CH3:22])[CH3:21])[CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 596053951-Azetidinecarboxylic acid, 3-(1-hydroxy-2-methylpropyl)-, 1,1-dimethylethyl ester

Product 1

HCID 59606118HCID 59606118, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3 mL) was added to a solution of 3-(1-hydroxy-2-methylpropyl)azetidine-1-carboxylic acid tert-butyl ester (0.84 g, 3.66 mmol) in dichloromethane (12 mL). The resulting reaction mixture was stirred at RT for 40 min. 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. The solvents were reduced in vacuo to afford 1-Azetidin-3-yl-2-methylpropan-1-ol as a white solid (0.42 g, 88%). 1H NMR (400 MHz, CDCl3): δ 3.63-3.62 (3H, m), 3.53-3.51 (2H, m), 2.88-2.87 (1H, m), 1.62-1.62 (1H, m), 0.89 (6H, dd, J=6.84, 4.72 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-00257d318be043548de0c237c7902407
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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