HCID 54248964, compound → HCID 54031485, compound

HRID 1767094Notes

Reaction equation

[CH3:1][Si](C=[N+]=[N-])(C)C.CCCCCC.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][C@@H:24]([CH2:27][CH2:28][C:29]([OH:31])=[O:30])[C@@H:23]([CH:32]=[CH2:33])[CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]>CO>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][C@@H:24]([CH2:27][CH2:28][C:29]([O:31][CH3:1])=[O:30])[C@@H:23]([CH:32]=[CH2:33])[CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 22 °C

Procedure

50 cm3 of a solution of 2M trimethylsilyldiazomethane/hexane are added, at a temperature in the region of 15° C., under an argon atmosphere, to 5 g (17.64 mmol) of (3R,4R)-1-tert-butyloxycarbonyl-4-(2-carboxyethyl)-3-vinylpiperidine in solution in 50 cm3 of methanol. After stirring for 3 hours at a temperature in the region of 22° C., the reaction medium is concentrated to dryness under reduced pressure (2.7 kPa) to give 5.3 g of (3R,4R)-1-tert-butyloxycarbonyl-4-(2-methoxycarbonylethyl)-3-vinylpiperidine in the form of an orange oil.

Workup

concentrationthe reaction medium is concentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record: ord-7705154a249748f68bfb118ed69a7bfc
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07232834B2

Reaction notes

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