Triethylamine → HCID 131728356, compound

HRID 1038015Notes

Reaction equation

HRID 1038015 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:11]([CH3:19])([CH3:18])[O:12][SiH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:10][CH2:9][NH:8][CH2:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1([C:11]([CH3:18])([CH3:19])[O:12][SiH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:10][CH2:9][N:8]([CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 131728355HCID 131728355, compound

Product 1

HCID 131728356HCID 131728356, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of 3-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidine-3-carboxylic acid ethyl ester (444 mg, 1.54 mmol), triethylamine (214 μl, 1.54 mmol) and cesium carbonate (251 mg, 0.77 mmol) in acetonitrile (5 ml) was added tert-butyl bromoacetate (351 μl, 2.38 mmol) slowly. The mixture was stirred for 1 hour, filtered and concentrated. The residue was diluted with ethyl acetate, washed with water and dried over MgSO4. Solvent was removed under reduced pressure to give a crude product that was purified by column chromatography on silica gel. Elution with a solution of ethyl acetate in hexanes (1:4) provided 580 mg (94%) of the title compound.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. customSolvent was removed under reduced pressure
  7. customto give a crude product that
  8. customwas purified by column chromatography on silica gel
  9. washElution with a solution of ethyl acetate in hexanes (1:4)

Sources & evidence

ORD record
ord-ef76eb0936b84d4295e4e4f3f9f4f8d9
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

Loading…