Imidazole → 1-(tert-Butyl) 3-methyl 5-((tert-butyldimethylsilyl)oxy)piperidine-1,3-dicarboxylate

HRID 57533Notes

Reaction equation

HRID 57533 reaction equation
[OH:1][CH:2]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5][CH:4]([C:15]([O:17][CH3:18])=[O:16])[CH2:3]1.N1C=CN=C1.[CH3:24][C:25]([Si:28](Cl)([CH3:30])[CH3:29])([CH3:27])[CH3:26]>ClCCl.CN(C1C=CN=CC=1)C>[Si:28]([O:1][CH:2]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:5][CH:4]([C:15]([O:17][CH3:18])=[O:16])[CH2:3]1)([C:25]([CH3:27])([CH3:26])[CH3:24])([CH3:30])[CH3:29]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 457909591-tert-Butyl 3-methyl 5-hydroxypiperidine-1,3-dicarboxylate

Product 1

HCID 711138811-(tert-Butyl) 3-methyl 5-((tert-butyldimethylsilyl)oxy)piperidine-1,3-dicarboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-tert-butyl 3-methyl 5-hydroxypiperidine-1,3-dicarboxylate (4.00 g, 15.4 mmol) in dichloromethane (40 mL) was subsequently added imidazole (1.26 g, 18.5 mmol), DMAP (0.38 g, 3.1 mmol), and TBDMS-Cl (2.79 g, 18.5 mmol). The reaction was stirred at room temperature for 40 h. The mixture was washed with HCl solution (1N), saturated sodium bicarbonate, and brine sequentially and dried over anhydrous sodium sulfate, filtrated, and concentrated to give the title compound. MS (m/z): 274 (M-Boc+H)+.

Workup

  1. washThe mixture was washed with HCl solution (1N), saturated sodium bicarbonate, and brine sequentially
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltrated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0eb9ffed99404ce0a69f4e7b2dca5bee
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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