Water → 1-tert-Butyl 3-methyl 4-(azetidin-1-yl)piperidine-1,3-dicarboxylate

HRID 2066502Notes

Reaction equation

HRID 2066502 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[C:10](=O)[CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6]1)=[O:4].[NH:19]1[CH2:22][CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl>[CH3:1][O:2][C:3]([CH:5]1[CH:10]([N:19]2[CH2:22][CH2:21][CH2:20]2)[CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6]1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 10422AzetidineHCID 5049666Sodium triacetoxyborohydrideHCID 112768931-tert-Butyl 3-methyl 4-oxopiperidine-1,3-dicarboxylate

Product 1

HCID 581170471-tert-Butyl 3-methyl 4-(azetidin-1-yl)piperidine-1,3-dicarboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-oxo-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (100 mg, 0.389 mmol) in DCE (11 mL) was added azetidine (33 mg, 0.578 mmol). The mixture was stirred at RT for 10 min, then sodium triacetoxyborohydride (132 mg, 0.623 mmol) was added and stirring was continued for 2 h. Water was added to the reaction mixture before being loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH then eluted with 2 M NH3 in MeOH to give the title compound as a colourless oil (102 mg, 88%).

Workup

  1. stirringstirring
  2. waitwas continued for 2 h
  3. washThe cartridge was washed with MeOH
  4. washthen eluted with 2 M NH3 in MeOH

Sources & evidence

ORD record
ord-599f909bfbe34005b7d1bd315b7b1479
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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