Methyl iodide → HCID 131729681, compound

HRID 1920160Notes

Reaction equation

[H-].[Na+].[C:3]([O:7][C:8]([N:10]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:11]1[CH:16]([OH:17])[CH2:15][CH2:14][N:13]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:12]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:35]I>C1COCC1>[C:31]([O:30][C:28]([N:10]([C:8]([O:7][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:9])[C@H:11]1[C@H:16]([O:17][CH3:35])[CH2:15][CH2:14][N:13]([C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])[CH2:12]1)=[O:29])([CH3:34])([CH3:33])[CH3:32]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of NaH (1.3 equiv.) in THF (0.1M) was added benzyl 3-(bis(tert-butoxycarbonyl)amino)-4-hydroxypiperidine-1-carboxylate (1.0 equiv.) and the reaction was heated to 50° C. for 10 min. Upon cooling to room temperature, MeI (1.5 equiv.) was added and the solution was allowed to stir for 16 h. The reaction was quenched with water, then extracted with EtOAc, the organic was dried with brine and Na2SO4, and concentrated. The crude material was purified via silica gel column chromatography eluting with EtOAc and hexanes (1:3) to give a clear oil in 71% yield. LCMS (m/z): 365.0 (MH+).

Workup

temperatureUpon cooling to room temperature
customThe reaction was quenched with water
extractionextracted with EtOAc
dry with materialthe organic was dried with brine and Na2SO4
concentrationconcentrated
customThe crude material was purified via silica gel column chromatography
washeluting with EtOAc and hexanes (1:3)
customto give a clear oil in 71% yield

Sources & evidence

ORD record: ord-4df3d6d969d64cd69e528d88159933e8
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168794B2

Reaction notes

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