Hydrochloric Acid → HCID 53662624, compound

HRID 975643Notes

Reaction equation

HRID 975643 reaction equation
[CH2:1]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].Cl>CN(C)C=O>[CH2:1]([N:8]1[CH2:12][C@H:11]([O:13][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH2:10][C@H:9]1[C:14]([O:16][CH3:17])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 11470360HCID 11470360, compound

Product 1

HCID 53662624HCID 53662624, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2S,4R)-1-benzyl-2-methoxycarbonyl-4-hydroxypyrrolidine (661 g) in N,N-dimethylformamide (3.3 l) were added successively imidazole (383 g) and t-butyldimethylsilyl chloride (508 g) at 10°~20° C. with stirring and the solution was stirred at ambient temperature for 3 hours. The mixture was poured into 0.1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with 5% aqueous sodium bicarbonate, water and 10% sodium chloride, dried with anhydrous magnesium sulfate and evaporated in vacuo to give (2S,4R)-1-benzyl -2-methoxycarbonyl-4-(t-butyldimethylsilyloxy)pyrrolidine (964 g).

Workup

  1. stirringthe solution was stirred at ambient temperature for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with 5% aqueous sodium bicarbonate, water and 10% sodium chloride
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-1b793835ff5a40e4b494710065a586c8
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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