tert-Butyl 3-(4-hydroxypiperidin-1-yl)azetidine-1-carboxylate → 1-(Azetidin-3-YL)piperidin-4-OL

HRID 1922669Notes

Reaction equation

HRID 1922669 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([N:12]2[CH2:17][CH2:16][CH:15]([OH: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][CH:15]([OH:18])[CH2:14][CH2:13]2)[CH2:9]1

Participants

3

Reactant 1

HCID 59605546tert-Butyl 3-(4-hydroxypiperidin-1-yl)azetidine-1-carboxylate

Product 1

HCID 220613791-(Azetidin-3-YL)piperidin-4-OLYield 94%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A 25 mL round-bottomed flask was charged with a solution of 3-(4-hydroxypiperidin-1-yl)azetidine-1-carboxylic acid tert-butyl ester (0.34 g, 1.33 mmol) in DCM/TFA (4 mL/4 mL). The reaction mixture was stirred for 7 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-ylpiperidin-4-ol as a colourless oil (0.194 g, 94%). 1H NMR (CDCl3, 400 MHz) δ 3.75-3.68 (m, 1H); 3.67-3.51 (m, 4H); 3.25-3.17 (m, 1H); 2.66-2.56 (m, 3H); 2.03-1.84 (m, 5H); 1.65-1.53 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-f963f83806414d96b1b521e804d465d4
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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