HCID 21080215, compound → HCID 13578534, compound

HRID 2212041Notes

Reaction equation

HRID 2212041 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:14])=O)(C)(C)C>ClCCl>[N:15]1([C:13]([C@@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[O:14])[CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

3

Reactant 1

HCID 21080215HCID 21080215, compound

Product 1

HCID 13578534HCID 13578534, compoundYield 132.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-2-(Pyrrolidin-1-ylcarbonyl)pyrrolidine-1-carboxylic acid tert-butyl ester (5.90 g, 22 mmol) was dissolved in dichloromethane (50 ml) Trifluoroacetic acid (30 ml) was added. The reaction mixture was stirred for 50 min at room temperature. The solvent was removed in vacuo. The residue was dissolved in a saturated aqueous solution of potassium carbonate (200 ml). It was extracted with dichloromethane (3×100 ml). The aqueous phase was saturated with sodium chloride and extracted with dichloromethane (3×200 ml). The combined organic layers were dried over magnesium sulphate. The solvent was removed in vacuo to give 4.89 g of the crude (pyrrolidin-1-yl)-((S)-pyrrolidin-2-yl)methanone, which was used in the next step without further purification.

Workup

  1. additionwas added
  2. customThe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in a saturated aqueous solution of potassium carbonate (200 ml)
  4. extractionIt was extracted with dichloromethane (3×100 ml)
  5. extractionextracted with dichloromethane (3×200 ml)
  6. dry with materialThe combined organic layers were dried over magnesium sulphate
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-667590909be1441eb2d312182f7c3fb9
Source dataset
uspto-grants-2006_09
Patent number
US07101898B2

Reaction notes

Loading…