Imidazole → HCID 57659768, compound

HRID 1011594Notes

Reaction equation

HRID 1011594 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.[OH:14][C@H:15]1[CH2:19][N:18]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[C@H:17]([C:33]([O:35][CH3:36])=[O:34])[CH2:16]1>CN(C=O)C>[Si:1]([O:14][C@H:15]1[CH2:19][N:18]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[C@H:17]([C:33]([O:35][CH3:36])=[O:34])[CH2:16]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 57659779HCID 57659779, compound

Product 1

HCID 57659768HCID 57659768, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

t-Butyldimethylsilyl chloride (TBSCl) (4.07 g, 27.03 mmol) and imidazole (2.58 g, 37.8 mmol) were added to a solution of (3) (9.55 g, 27.03 mmol) in DMF (60 ml) at RT. The reaction was stirred for 4 hours and concentrated in vacuo. The residue was dissolved in EtOAc and washed with 0.1M aqueous HCl, sat. sodium bicarbonate solution and brine. The organic layers were dried with sodium sulfate and concentrated in vacuo to yield (2S,4R)-methyl 4-(tert-butyldimethylsilyloxy)-1-(4-(trifluoromethyl)phenylsulfonyl)pyrrolidine-2-carboxylate (4) (11.83 g, 94%) as a yellow oil. It was used without further purification in the next step. MS m/z 490.2. (M+Na)+; retention time=3.159 min, method [1].

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with 0.1M aqueous HCl, sat. sodium bicarbonate solution and brine
  4. dry with materialThe organic layers were dried with sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dfd0c3bcf2ba40368715bf2928560ebd
Source dataset
uspto-grants-2011_07
Patent number
US07977368B2

Reaction notes

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