Reaction #710531

ord-eec1b9c0cf7f4088aed943b49beea7bb

Reaction equation

CS(=O)(=O)O
Methanesulfonic acid
CC(C)(C)OC(=O)N1CCC[C@H](C(=O)O)C1
(S)—N-(tert-butoxycarbonyl)nipecotic acid
→
COC(=O)[C@H]1CCCNC1
(S)-methyl nipecotate

Reactants

CS(=O)(=O)O
Methanesulfonic acid
CC(C)(C)OC(=O)N1CCC[C@H](C(=O)O)C1
(S)—N-(tert-butoxycarbonyl)nipecotic acid

Reagents

None

Solvents

CO
methanol

Conditions

Temperature
25°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09302980B2uspto-grants-2016_04