Imidazole → [4-(tert-Butyl-diphenyl-silanyloxy)-piperidin-1-yl]-acetic acid methyl ester

HRID 1670827Notes

Reaction equation

HRID 1670827 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]1.N1C=CN=C1.[Si:18](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OCC)C>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([O:11][Si:18]([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 94078tert-ButyldiphenylchlorosilaneHCID 28837753Methyl 2-(4-hydroxypiperidin-1-yl)acetate

Product 1

HCID 67354799[4-(tert-Butyl-diphenyl-silanyloxy)-piperidin-1-yl]-acetic acid methyl esterYield 73.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Treat a solution of (4-hydroxy-piperidin-1-yl)-acetic acid methyl ester (10.0 g, 57.7 mmol) and imidazole (4.71 g, 69.2 mmol) in DMF (100 mL) with t-butyl-diphenylsilyl chloride (19.04 g, 69.3 mmol) and stir for 16 hours at room temperature. Dilute the reaction with diethyl ether and wash with water. Dry the organic layer (Na2SO4), remove the solvent in vacuo to afford crude product, and purify with a 2% methanol in CH2Cl2 to afford 17.38 g (73%) of the titled product. Rf=0.71 (9/1 CH2Cl2/methanol). ES MS (m/z): 412 (M+).

Workup

  1. additionDilute
  2. washwash with water
  3. dry with materialDry the organic layer (Na2SO4)
  4. customremove the solvent in vacuo
  5. customto afford crude product
  6. custompurify with a 2% methanol in CH2Cl2

Sources & evidence

ORD record
ord-ebf8026e3f0749868a1c83c7fe7b5cfd
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

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