Water → HCID 101175890, compound

HRID 1034641Notes

Reaction equation

C[Mg]Br.[C:4]1(C)C=CC=CC=1.[CH2:11]([O:13][P:14]([N:19]1[CH:25]2[CH:20]1[CH2:21][CH2:22][N:23]([C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])[CH2:24]2)([O:16][CH2:17][CH3:18])=[O:15])[CH3:12].O>C1COCC1>[CH2:11]([O:13][P:14]([NH:19][C@H:25]1[C@H:20]([CH3:4])[CH2:21][CH2:22][N:23]([C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[CH2:24]1)([O:16][CH2:17][CH3:18])=[O:15])[CH3:12]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of Cu(I)I (0.10 g, 0.54 mmol) in THF (20 mL) was slowly added 1.40M methylmagnesium bromide (15.5 mL, 21.7 mmol) in 3:1 toluene:THF at −30° C. After stirring at that temperature for 15 minutes, a solution of benzyl 7-(diethoxyphosphoryl)-3,7-diazabicyclo[4.1.0]heptane-3-carboxylate (2.00 g, 5.43 mmol, Example H, Step D) in THF (10 mL) was added at −30° C. The mixture was then slowly warmed to 0° C. in 2 hours and stirred at 0° C. for 2 hours. Water (20 mL) was added and extracted with ethyl acetate (2×30 mL), washed with brine, dried (sodium sulfate) and concentrated in vacuo. The residue obtained was purified by flash chromatography on silica gel (ethyl acetate) to give trans-benzyl 3-(diethoxyphosphorylamino)-4-methylpiperidine-1-carboxylate (1.00 g, 48%) as an oil.

Workup

customat −30° C
stirringstirred at 0° C. for 2 hours
extractionextracted with ethyl acetate (2×30 mL)
washwashed with brine
dry with materialdried (sodium sulfate)
concentrationconcentrated in vacuo
customThe residue obtained
customwas purified by flash chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record: ord-b814055c170740f6998f9a426d8c6a36
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08545897B2

Reaction notes

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