Methanesulfonic Acid → Nipecotic acid, S-(+)-

HRID 623350Notes

Reaction equation

HRID 623350 reaction equation
CS(O)(=O)=O.C(OC([N:13]1[CH2:21][CH2:20][CH2:19][C@H:15]([C:16]([OH:18])=[O:17])[CH2:14]1)=O)(C)(C)C.C(N(CC)CC)C>C(Cl)Cl>[NH:13]1[CH2:21][CH2:20][CH2:19][C@H:15]([C:16]([OH:18])=[O:17])[CH2:14]1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8471TriethylamineHCID 6951168(3S)-1-((tert-butoxy)carbonyl)piperidine-3-carboxylic acid

Product 1

HCID 6575389Nipecotic acid, S-(+)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Methanesulfonic acid (576 mg, 6 mmol) was added to a solution of (S)—N-(tert-butoxycarbonyl)nipecotic acid (1145 mg, 5 mmol) and methylene chloride (5 mL), and the mixture was stirred at 25° C. for 16 hours. Triethylamine (708 mg, 7 mmol) was added thereto, and then solid was precipitated. The solid was sufficiently precipitated, and then the solution was stirred at 25° C. for 30 minutes. Thereafter, the solid was separated by filtration under reduced pressure. The solid was washed with methylene chloride (5 mL), and then was subjected to vacuum drying. Thereby, the titled compound was produced as a white solid (238 mg, yield of 37%).

Workup

  1. customsolid was precipitated
  2. customThe solid was sufficiently precipitated
  3. stirringthe solution was stirred at 25° C. for 30 minutes
  4. customThereafter, the solid was separated by filtration under reduced pressure
  5. washThe solid was washed with methylene chloride (5 mL)
  6. customdrying

Sources & evidence

ORD record
ord-1a7fd1c2999b4aaa89245faa1cdccc57
Source dataset
uspto-grants-2016_04
Patent number
US09302980B2

Reaction notes

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