Imidazole → HCID 22993442, compound

HRID 1860405Notes

Reaction equation

HRID 1860405 reaction equation
[OH:1][CH:2]([CH3:10])[C:3]([N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].N1C=CN=C1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:19]([Si:16]([CH3:18])([CH3:17])[O:1][CH:2]([CH3:10])[C:3]([N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4])([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 14373622HCID 14373622, compound

Product 1

HCID 22993442HCID 22993442, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-hydroxy-1-pyrrolidin-1-yl-propan-1-one (47.0 mmol, 6.72 g) in DMF (25 mL) was added imidazole (70.5 mmol, 4.8 g), N,N-dimethyl-4-aminopyridine (4.7 mmol, 0.57 g) at room temperature. tert-Butyl-dimethylsilyl chloride (48.5 mmol, 7.31 g) was then added while stirring. Some exotherm was observed. The initial pale yellow solution turned brown-red in color and some precipitate was observed after 30 min. The reaction mixture was stirred overnight and was then filtered through a sintered glass funnel. The solid was washed with Et2O. The filtrate was diluted with water (150 mL) and it was extracted with Et2O (2×100 mL). The organic extracts were combined and washed successively with water (100 mL), saturated NH4Cl solution, and the organic layer was separated. It was dried over Na2SO4, filtered, and the solvent was removed in vacuo to obtain 2-(tert-butyl-dimethyl-silanyloxy)-1-pyrrolidin-1-yl-propan-1-one as a golden yellow oil (10.4 g, 86% yield). The product was judged to be >95% pure by NMR and was used in next step without any purification.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. filtrationwas then filtered through a sintered glass funnel
  3. washThe solid was washed with Et2O
  4. additionThe filtrate was diluted with water (150 mL) and it
  5. extractionwas extracted with Et2O (2×100 mL)
  6. washwashed successively with water (100 mL), saturated NH4Cl solution
  7. customthe organic layer was separated
  8. dry with materialIt was dried over Na2SO4
  9. filtrationfiltered
  10. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-024d984e839f4458a84775c762a6978e
Source dataset
uspto-grants-2003_03
Patent number
US06531471B2

Reaction notes

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