Sodium Carbonate → HCID 59026150, compound

HRID 639094Notes

Reaction equation

HRID 639094 reaction equation
[C:1]([C:3]1(O)[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4]1)#[N:2].CCN(S(F)(F)[F:25])CC.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:1]([C:3]1([F:25])[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4]1)#[N:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 123472(Diethylamino)sulfur trifluorideHCID 59026120HCID 59026120, compound

Product 1

HCID 59026150HCID 59026150, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of phenylmethyl 3-cyano-3-hydroxy-1-pyrrolidinecarboxylate (1.8 g, 7.31 mmole), in DCM (50 mL) at −78° C. was added DAST dropwise (0.98 mL, 8.04 mmole). After 2 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 (1.0 g, 55%) as a light orange oil: LC-MS (ES) m/e 249 (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-2444ca7b1bba405893ce2153bc95737f
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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