Imidazole → HCID 66704803, compound

HRID 424735Notes

Reaction equation

HRID 424735 reaction equation
[CH:1]1([NH:4][C:5]([C@@H:7]2[C@H:11]([CH2:12][OH:13])[CH2:10][N:9]([C@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:15])[CH2:8]2)=[O:6])[CH2:3][CH2:2]1.N1C=CN=C1.[C:27]([Si:31](Cl)([CH3:33])[CH3:32])([CH3:30])([CH3:29])[CH3:28]>CN(C)C=O>[CH:1]1([NH:4][C:5]([C@@H:7]2[C@H:11]([CH2:12][O:13][Si:31]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:33])[CH3:32])[CH2:10][N:9]([C@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:15])[CH2:8]2)=[O:6])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 66705180HCID 66705180, compound

Product 1

HCID 66704803HCID 66704803, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(3R,4S)—N-Cyclopropyl-4-hydroxymethyl-1-[(1S)-1-phenylethyl]pyrrolidine-3-carboxamide (7.54 g) was dissolved in N,N-dimethylformamide (180 mL). While this solution was chilled in an ice water bath, imidazole (2.67 g) and then tert-butylchlorodimethylsilane (4.72 g) were added. The mixture was stirred at room temperature for 90 min and was subsequently concentrated under reduced pressure. The residue was dissolved in ethyl acetate (300 mL), washed with water (2×100 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluant: ethyl acetate) to give (3R,4S)—N-cyclopropyl-4-(tert-butyldimethylsilyl)oxymethyl-1-[(1S)-1-phenylethyl]pyrrolidine-3-carboxamide as a pale yellow tar (7.05 g).

Workup

  1. temperatureWhile this solution was chilled in an ice water bath
  2. concentrationwas subsequently concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (300 mL)
  4. washwashed with water (2×100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluant: ethyl acetate)

Sources & evidence

ORD record
ord-ac3996a964314ca39d5b8ddddf57ec28
Source dataset
uspto-grants-2012_01
Patent number
US08106072B2

Reaction notes

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