Sodium Carbonate → HCID 86616803, compound

HRID 639100Notes

Reaction equation

HRID 639100 reaction equation
[C:1]([C@H:3]1[C@H:7](O[Si](C)(C)C)[CH2:6][N:5]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:4]1)#[N:2].CCN(S(F)(F)[F:26])CC.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:1]([C@H:3]1[C@@H:7]([F:26])[CH2:6][N:5]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:4]1)#[N:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 123472(Diethylamino)sulfur trifluorideHCID 86616804HCID 86616804, compound

Product 1

HCID 86616803HCID 86616803, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (±)-1,1-dimethylethyl trans-3-cyano-4-[(trimethylsilyl)oxy]-1-pyrrolidinecarboxylate (1.0 g, 3.52 mmole), in DCM (50 mL) at −78° C. was added DAST dropwise (0.90 mL, 7.40 mmole). After 3 h, Aqueous Na2CO3 was added to the reaction solution and the layers separated. The organic layer was dried over Na2SO4 and concentrated under vacuum. Purification on silica (hexanes/EtOAc, 1:1) provided the title compound (0.51 g, 67%) as a colorless oil: LC-MS (ES) m/e 215 (M+H)+.

Workup

  1. customthe layers separated
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customPurification on silica (hexanes/EtOAc, 1:1)

Sources & evidence

ORD record
ord-2f6b664c83064606ad30cd37a12cc85b
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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