1,1-Dibromoethane → HCID 66850126, compound

HRID 1914577Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([OH:14])[C@@H:9]1[OH:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Br[CH:19](Br)[CH3:20]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]2[O:14][CH2:19][CH2:20][O:15][CH:9]12)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 55 °C

Procedure

cis-2,3-Dihydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.246 g, 1.13 mmol) was dissolved in dibromoethane (1.7 mL) and tetrabutyl ammonium bromide (71 mg, 2.2 mmol) was added. Sodium hydroxide (50% aqueous solution, 17.8 g) was added slowly over 10 minutes at 50° C. A further amount of dibromoethane (7.4 mL, 105.5 mmol in total) was added and the mixture was heated at 55° C. overnight. Dibromoethane (3 mL) was added and the mixture was heated at 55° C. for a further 4 hours and then diluted with water and extracted with DCM (×2). The organics were washed with brine then dried over sodium sulfate, filtered and evaporated. The crude material was purified by chromatography on a 5 g silica II cartridge, eluting with 10-33% diethyl ether in pentane to afford hexahydro-[1,4]dioxino[2,3-b]pyridine-5-carboxylic acid tert-butyl ester as an off-white oil (0.106 g).

Workup

temperaturethe mixture was heated at 55° C. for a further 4 hours
extractionextracted with DCM (×2)
washThe organics were washed with brine
dry with materialthen dried over sodium sulfate
filtrationfiltered
customevaporated
customThe crude material was purified by chromatography on a 5 g silica II cartridge
washeluting with 10-33% diethyl ether in pentane

Sources & evidence

ORD record: ord-4c5e164d5c574878b4a9a0b21cc4deff
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614209B2

Reaction notes

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