Methanesulfonic Acid → (S)-Methyl piperidine-3-carboxylate

HRID 623349Notes

Reaction equation

HRID 623349 reaction equation
[CH3:1]S(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>CO>[NH:13]1[CH2:21][CH2:20][CH2:19][C@H:15]([C:16]([O:18][CH3:1])=[O:17])[CH2:14]1

Participants

4

Reactant 2

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

Product 1

HCID 18727136(S)-Methyl piperidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 methanol (5 mL). When the mixture was stirred at 25° C. for 16 hours, (S)-methyl nipecotate was produced, and the object (S)-nipecotic acid was not produced.

Sources & evidence

ORD record
ord-eec1b9c0cf7f4088aed943b49beea7bb
Source dataset
uspto-grants-2016_04
Patent number
US09302980B2

Reaction notes

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