HCID 22061396, compound → HCID 21029908, compound

HRID 1945527Notes

Reaction equation

HRID 1945527 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([N:12]2[CH2:17][CH2:16][C:15]([OH:19])([CH3:18])[CH2:14][CH2:13]2)[CH2:9]1)=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH:8]1[CH2:11][CH:10]([N:12]2[CH2:17][CH2:16][C:15]([CH3:18])([OH:19])[CH2:14][CH2:13]2)[CH2:9]1

Participants

3

Reactant 1

HCID 22061396HCID 22061396, compound

Product 1

HCID 21029908HCID 21029908, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A 25 mL round-bottomed flask was charged with a solution of 3-(4-hydroxy-4-methylpiperidin-1-yl)azetidine-1-carboxylic acid tert-butyl ester (0.2 g, 0.74 mmol) in DCM/TFA (3 mL/3 mL). The reaction mixture was stirred for 4 h at room temperature. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the desired product was eluted using 2 M NH3 in MeOH to give 1-Azetidin-3-yl-4-methylpiperidin-4-ol as a colourless oil (0.107 g, 85%). 1H NMR (CDCl3, 400 MHz) δ 3.61 (t, J=7.3 Hz, 2 H); 3.54 (t, J=7.3 Hz, 2 H); 3.29-3.15 (m, 1 H); 3.04 (s, 2 H); 2.40 (d, J=10.8 Hz, 2 H); 2.30-2.18 (m, 2 H); 1.67-1.56 (m, 4 H); 1.23 (s, 3 H).

Workup

  1. washThe cartridge was washed with MeOH
  2. washthe desired product was eluted

Sources & evidence

ORD record
ord-49ea83c2436c485f8071e6a8620797ac
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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