Thioglycolic Acid → (2S,5R)-1-tert-butyl 2-ethyl 5-((benzyloxy)amino)piperidine-1,2-dicarboxylate

HRID 1855549Notes

Reaction equation

O[Li].O.SCC(O)=O.[CH2:9]([O:16][N:17]([C@H:30]1[CH2:35][N:34]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C@H:33]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:32][CH2:31]1)S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN(C=O)C.O>[CH2:9]([O:16][NH:17][C@H:30]1[CH2:35][N:34]([C:36]([O:38][C:39]([CH3:41])([CH3:42])[CH3:40])=[O:37])[C@H:33]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:32][CH2:31]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 20 °C

Procedure

LiOH.H2O (95 g, 2.3 mol) and 2-mercaptoacetic acid (124 g, 1.3 mol) were added to a solution of (2S,5R)-1-tert-butyl 2-ethyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)piperidine-1,2-dicarboxylate (251 g, 0.45 mol) in DMF (1200 mL). The reaction mixture was then stirred at 20° C. overnight. The reaction mixture was diluted with water and extracted with EtOAc (3×). The combined organic layer was washed with brine (3×), concentrated in vacuum and purified by silica gel column chromatography (3:1 petroleum ether/EtOAc) to afford (2S,5R)-1-tert-butyl 2-ethyl 5-((benzyloxy)amino)piperidine-1,2-dicarboxylate (122.9 g, 85%) as a yellow solid.

Workup

extractionextracted with EtOAc (3×)
washThe combined organic layer was washed with brine (3×)
concentrationconcentrated in vacuum
custompurified by silica gel column chromatography (3:1 petroleum ether/EtOAc)

Sources & evidence

ORD record: ord-9ca5af69b53846a380cd427b5d2b6e32
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962844B2

Reaction notes

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