Imidazole → HCID 54561970, compound

HRID 1856705Notes

Reaction equation

HRID 1856705 reaction equation
[CH2:1]([O:8][C@H:9]([CH3:20])[CH:10]([OH:19])[C:11]#[C:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].N1C=CN=C1.O>CN(C)C=O>[CH2:1]([O:8][C@H:9]([CH3:20])[CH:10]([O:19][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[C:11]#[C:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 53661647HCID 53661647, compound

Product 1

HCID 54561970HCID 54561970, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(3RS,4R)-4-Benzyloxy-1-pyridin-3-yl-pent-1-yn-3-ol (Example 30b), 1.745 g) was stirred in dimethylformamide (20 ml) with tert-butyldimethylsilyl chloride (1.18 g) and imidazole (0.89 g) at room temperature for 22 hours. Water was added and the reaction was extracted with diethyl ether. The organic phases were combined, washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 4:1 isohexane/ethyl acetate gave the subtitle compound as an oil (2.014 g).

Workup

  1. extractionthe reaction was extracted with diethyl ether
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel
  7. washeluting with 4:1 isohexane/ethyl acetate

Sources & evidence

ORD record
ord-f895de0f4f384048b616889650d7fbec
Source dataset
uspto-grants-2000_11
Patent number
US06143751

Reaction notes

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