Trifluoroacetic acid → HCID 59606104, compound

HRID 1945512Notes

Reaction equation

HRID 1945512 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([N:12]2[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13]2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:11][CH:10]([N:12]2[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13]2)[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59605396HCID 59605396, compound

Product 1

HCID 59606104HCID 59606104, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-((S)-3-hydroxypyrrolidin-1-yl)azetidine-1-carboxylic acid tert-butyl ester (390 mg, 1.61 mmol) and TFA (2 mL) in DCM (4 mL) was stirred at room temperature for 2 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH/DCM and the product eluted with 2M NH3/MeOH affording the title compound as a white solid (244 mg, quant.). 1H NMR (CDCl3, 300 MHz): δ 4.40-4.33 (m, 1 H); 3.70-3.60 (m, 4 H); 3.44-3.34 (m, 1 H); 2.88-2.77 (m, 1 H); 2.73-2.52 (m, 3 H); 2.47 (dd, J=10.1, 5.2 Hz, 1 H); 2.30-2.12 (m, 2 H); 1.84-1.69 (m, 1 H).

Workup

  1. washwas washed with MeOH/DCM
  2. washthe product eluted with 2M NH3/MeOH affording the title compound as a white solid (244 mg, quant.)

Sources & evidence

ORD record
ord-33908dc3f394490b8c607057a7048315
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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