3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → HCID 22061396, compound

HRID 1922676Notes

Reaction equation

HRID 1922676 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10](=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:13][C:14]1([OH:20])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([N:17]2[CH2:18][CH2:19][C:14]([OH:20])([CH3:13])[CH2:15][CH2:16]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 156491744-Methylpiperidin-4-ol

Product 1

HCID 22061396HCID 22061396, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A 50 mL round-bottomed flask was charged with a solution of 3-oxoazetidine-1-carboxylic acid tert-butyl ester (0.57 g, 3.33 mmol), 4-methylpiperidin-4-ol (0.46 g, 3.99 mmol) and 4 Å molecular sieves (3.34 g) in DCE (20 mL) The reaction mixture was stirred for 6 h at room temperature. Sodium triacetoxyborohydride (1.41 g, 6.66 mmol) was added and the reaction mixture was stirred for 18 h at room temperature. The suspension was filtered through Celite and the solution was concentrated in vacuo. The residue was purified by flash chromatography (Si—PPC, EtOAc:cyclohexane, 0:100 to 100:0) to give 3-(4-Hydroxy-4-methylpiperidin-1-yl)azetidine-1-carboxylic acid tert-butyl ester as a colourless oil (0.49 g, 55%). 1H NMR (CDCl3, 400 MHz) δ 3.93 (dd, J=8.7, 7.17 Hz, 2H); 3.82 (dd, J=8.7, 5.5 Hz, 2H); 3.15-3.07 (m, 1H); 2.58-2.44 (m, 2H); 2.27 (td, J=11.0, 3.5 Hz, 2H); 1.77-1.54 (m, 4H); 1.42 (s, 9H); 1.26 (t, J=6.7 Hz, 3H).

Workup

  1. stirringthe reaction mixture was stirred for 18 h at room temperature
  2. filtrationThe suspension was filtered through Celite
  3. concentrationthe solution was concentrated in vacuo
  4. customThe residue was purified by flash chromatography (Si—PPC, EtOAc:cyclohexane, 0:100 to 100:0)

Sources & evidence

ORD record
ord-3462ef89652a48f1b54a9159261afcc8
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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