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

HRID 1620376Notes

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

14.4 ml (104 mmol) of triethylamine are added to a solution of 8.0 g (31 mmol) of commercial methyl (S)-2-amino-3-tert-butoxycarbonylaminopropanoate hydrochloride in 160 ml of tert-butanol, and then the reaction medium is stirred for 30 min at 40° C., and filtered in order to remove the triethylammonium salts. 6 ml (44 mmol) of 1,5-dibromopentane are added to the filtrate thus obtained, and the reaction medium is heated at 80° C. for 3 days. After the insoluble material has been filtered off, the filtrate is concentrated under vacuum. The crude residue is purified by chromatography on silica gel, elution being carried out with a 70/30 heptane/ethyl acetate mixture. 5.3 g (59%) of methyl(S)-3-tert-butoxycarbonylamino-2-piperidin-1-ylpropanoate are obtained in the form of a colorless oil.

Workup

filtrationfiltered in order
customto remove the triethylammonium salts
customthus obtained
temperaturethe reaction medium is heated at 80° C. for 3 days
filtrationAfter the insoluble material has been filtered off
concentrationthe filtrate is concentrated under vacuum
customThe crude residue is purified by chromatography on silica gel, elution

Sources & evidence

ORD record: ord-3ae1e6cb501e411887a921d4cbe7afb6
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772478B2

Reaction notes

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