Tin tetrachloride → HCID 66757079, compound

HRID 1642717Notes

Reaction equation

HRID 1642717 reaction equation
CO[CH:3]1[N:7]([C:8]([O:10][CH3:11])=[O:9])[C@H:6]([C:12]([O:14][CH3:15])=[O:13])[CH2:5][CH2:4]1.C[Si]([C:20]#[C:21][CH3:22])(C)C.[Sn](Cl)(Cl)(Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[CH:20]([C@@H:3]1[N:7]([C:8]([O:10][CH3:11])=[O:9])[C@H:6]([C:12]([O:14][CH3:15])=[O:13])[CH2:5][CH2:4]1)=[CH:21][CH3:22]

Participants

6

Reactant 4

HCID 24287Tin tetrachlorideHCID 803631-(Trimethylsilyl)prop-1-yneHCID 6451240Aluminum(III) ChlorideHCID 11053097Dimethyl (2S)-5-methoxypyrrolidine-1,2-dicarboxylate

Product 1

HCID 66757079HCID 66757079, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold −45° C. solution of dimethyl (2S)-5-methoxypyrrolidine-1,2-dicarboxylate (10 g, 46.08 mmol, Example 1B) and trimethylsilylpropyne (14.24 ml, 92.16 mmol, 2.0 equiv) in methylene chloride (180 mL) was added a solution of tin (IV) chloride (1 Min methylene chloride, 60.0 mL, 60.0 mmol, 1.3 equiv) dropwise via an addition funnel over 30 minutes. To the dark yellow solution was added solid aluminum chloride (8.58 g, 64.52 mmol, 1.4 equiv) in one portion. The resulting mixture was allowed to warm to room temperature and stirred at room temperature for 48 hours. The reaction mixture was carefully quenched by saturated aqueous NH4OH (100 mL) with ice cooling. A white precipitate formed and was removed by filtration. The crude product was obtained after concentration. The residue was chromatographed on a Biotage flash 40 M eluting with 70% hexane/30% ethyl acetate to afford the titled compound. MS (DCI/NH3) m/e 226 (M+H)+.

Workup

  1. customThe reaction mixture was carefully quenched by saturated aqueous NH4OH (100 mL) with ice cooling
  2. customA white precipitate formed
  3. customwas removed by filtration
  4. customThe crude product was obtained
  5. concentrationafter concentration
  6. customThe residue was chromatographed on a Biotage flash 40 M
  7. washeluting with 70% hexane/30% ethyl acetate

Sources & evidence

ORD record
ord-3729817ea5ec4882917863c60b7f2e0d
Source dataset
uspto-grants-2012_02
Patent number
US08119664B2

Reaction notes

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