Methanesulfonic Acid → 2-Methyl-L-proline

HRID 623353Notes

Reaction equation

HRID 623353 reaction equation
CS(O)(=O)=O.C(OC([N:13]1[CH2:20][CH2:19][CH2:18][C@@:14]1([CH3:21])[C:15]([OH:17])=[O:16])=O)(C)(C)C.C(N(CC)CC)C>ClCCCl>[CH3:21][C@@:14]1([C:15]([OH:17])=[O:16])[CH2:18][CH2:19][CH2:20][NH:13]1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8471TriethylamineHCID 11206950(2S)-1-(tert-Butoxycarbonyl)-2-methylpyrrolidine-2-carboxylic acid

Product 1

HCID 69936642-Methyl-L-proline

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
25 °C

Procedure

Methanesulfonic acid (252 mg, 2.6 mmol) was added to a solution of (S)—N-(tert-butoxycarbonyl)-2-methylproline (500 mg, 2.2 mmol) and 1,2-dichloroethane (2.53 g), and the mixture was stirred at 25° C. for 3 hours. When triethylamine (265 mg, 2.6 mmol) was added thereto, a solid was precipitated. The solid was sufficiently precipitated, and then the solution was stirred at 25° C. for 30 minutes and further stirred at 25° C. for 2 hours. Thereafter, the solid was then separated by filtration under reduced pressure. The solid was washed with 1,2-dichloroethane (0.2 mL), and then was subjected to vacuum drying. Thereby, the titled compound was produced as a white solid (197 mg, yield of 69%).

Workup

  1. customa solid was precipitated
  2. customThe solid was sufficiently precipitated
  3. stirringthe solution was stirred at 25° C. for 30 minutes
  4. stirringfurther stirred at 25° C. for 2 hours
  5. customThereafter, the solid was then separated by filtration under reduced pressure
  6. washThe solid was washed with 1,2-dichloroethane (0.2 mL)
  7. customdrying

Sources & evidence

ORD record
ord-dd5278d7a5ae40de88fa47dff3132cbf
Source dataset
uspto-grants-2016_04
Patent number
US09302980B2

Reaction notes

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