Phosphoric Acid → HCID 18957101, compound

HRID 2379423Notes

Reaction equation

[N:1]12[CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]=[C:3]([C:9](N(OC)C)=[O:10])[CH2:2]2.[CH3:15][Li].[Br-].[Li+].P(=O)(O)(O)O>O1CCCC1.C(OCC)C>[C:9]([C:3]1[CH2:2][N:1]2[CH2:8][CH:5]([CH:4]=1)[CH2:6][CH2:7]2)(=[O:10])[CH3:15]

Participants

Conditions

Temperature: -70 °C

Procedure

A solution of (±)1-azabicyclo[3.2.1]oct-3-en-3-yl-N-methoxy-N-methylcarboxamide (D8) (0.40 g, 2.0 mmole) in dry tetrahydrofuran (20 ml) was cooled to -70° C., under a nitrogen atmosphere, and treated dropwise over 15 minutes with methyllithium (1.47 ml of a 1.5 m solution in diethyl ether as the complex with lithium bromide, 2.2 mmole). The temperature was maintained at -70° C. for 30 minutes, and then allowed to warm to 0° C. over 1.75h. The reaction was cooled to -20° C. and poured into a 1M solution of orthophosphoric acid (20 ml) cooled below 0° C. The organic layer was separated, and the aqueous phase was saturated with potassium carbonate, and extracted exhaustively with chloroform. The combined organic extracts were dried (Na2SO4) and concentrated in vacuo to give a pale yellow oil (0.33 g) which was distilled in a kugelrohr at 150° C./0.1 mmHg to give the title compound (D10) as a colourless liquid (0.28 g, 93%).

Workup

temperatureto warm to 0° C. over 1.75h
temperatureThe reaction was cooled to -20° C.
temperaturecooled below 0° C
customThe organic layer was separated
extractionextracted exhaustively with chloroform
dry with materialThe combined organic extracts were dried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-dfca97e3a355493b8eca1c3a6d06ed37
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05362739

Reaction notes

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