Ethyl (S)-2-(Boc-amino)-6-diazo-5-oxohexanoate → (S)-1-tert-butyl 2-ethyl 5-oxopiperidine-1,2-dicarboxylate

HRID 2272844Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:15][CH2:16][C:17](=[O:21])[CH:18]=[N+]=[N-])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl>[O:21]=[C:17]1[CH2:18][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C@H:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:15][CH2:16]1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of (S)-ethyl 2-((tert-butoxycarbonyl)amino)-6-diazo-5-oxohexanoate (350 g, 1.18 mol) in DCM (1500 mL) was added to a solution of Rh2(OAc)4 (3.5 g, 7.9 mmol) in DCM (750 mL) at 0° C. The reaction was then stirred at 20° C. overnight and then concentrated in vacuum. The crude sample was purified by silica gel column chromatography (5:1 petroleum ether/EtOAc) to afford (S)-1-tert-butyl 2-ethyl 5-oxopiperidine-1,2-dicarboxylate (175.9 g, 55%) as a yellow oil.

Workup

concentrationconcentrated in vacuum
customThe crude sample was purified by silica gel column chromatography (5:1 petroleum ether/EtOAc)

Sources & evidence

ORD record: ord-102ec1e3e9de44da8dbad2cb2b032bc9
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120795B2

Reaction notes

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