Trifluoroacetic acid → HCID 59605554, compound

HRID 1945577Notes

Reaction equation

HRID 1945577 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:18][CH:17]([C:19]([N:21]2[CH2:25][CH2:24][C@@H:23]([OH:26])[CH2:22]2)=[O:20])[CH2:16]1)=O)(C)(C)C>ClCCl>[NH:15]1[CH2:18][CH:17]([C:19]([N:21]2[CH2:25][CH2:24][C@@H:23]([OH:26])[CH2:22]2)=[O:20])[CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59605224HCID 59605224, compound

Product 1

HCID 59605554HCID 59605554, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3 mL) was added to a solution of 3-((R)-3-hydroxypyrrolidine-1-carbonyl)azetidine-1-carboxylic acid tert-butyl ester (420 mg, 1.55 mmol) in dichloromethane (12 mL) The resulting reaction mixture was stirred at RT for 2 h. The solvents were reduced in vacuo. The resulting residue was loaded onto an Isolute® SCX-2 cartridge (10 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-yl-((R)-3-hydroxypyrrolidin-1-yl)methanone as colourless oil (225 mg, 85%). 1H NMR (400 MHz, DMSO, d6): δ 4.26-4.22 (1 H, m), 3.47-3.44 (10 H, m), 2.13-2.09 (1 H, m), 1.81 (2 H, m)

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-939698fc78ef4671bc7b8cf0105c3021
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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