1,5-Dibromopentane → methyl(S)-3-tert-butoxycarbonylamino-2-piperidin-1-ylpropanoate

HRID 1777268Notes

Reaction equation

C(N(CC)CC)C.Cl.[NH2:9][C@@H:10]([CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:11]([O:13][CH3:14])=[O:12].Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]Br>C(O)(C)(C)C>[C:20]([O:19][C:17]([NH:16][CH2:15][C@H:10]([N:9]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[C:11]([O:13][CH3:14])=[O:12])=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 40 °C

Procedure

1.8 ml (6.5 mmol) of triethylamine are added to a solution of 1 g (6.5 mmol) of commercial methyl (S)-2-amino-3-tert-butoxycarbonylaminopropanoate hydrochloride in 20 ml of tert-butanol. The reaction medium is stirred for 30 min at 40° C. then filtered. Added to the filtrate thus obtained are 1.2 ml (8.6 mmol) of 1,5-dibromopentane and the reaction medium is heated at 60° C. for 3 days. After filtration of the insoluble fraction, the filtrate is concentrated under vacuum. The crude residue is purified by chromatography over silica gel eluted with a 70/30 heptane/ethyl acetate mixture. 600 mg (49%) of methyl (S)-3-tert-butoxycarbonylamino-2-piperidin-1-yl-propanoate are obtained in the form of a colourless oil.

Workup

filtrationthen filtered
additionAdded to the filtrate
customthus obtained
temperaturethe reaction medium is heated at 60° C. for 3 days
filtrationAfter filtration of the insoluble fraction
concentrationthe filtrate is concentrated under vacuum
customThe crude residue is purified by chromatography over silica gel
washeluted with a 70/30 heptane/ethyl acetate mixture

Sources & evidence

ORD record: ord-40f75cfcc5fc4cbcbb9ab9ce57de8ac0
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266848B2

Reaction notes

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