Benzyl 11-(methoxy(methyl)amino)-11-oxoundecylcarbamate → Benzyl 11-oxododecylcarbamate

HRID 2188804Notes

Reaction equation

HRID 2188804 reaction equation
CON(C)[C:4](=[O:26])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH3:28][Mg]Cl>C1COCC1>[O:26]=[C:4]([CH3:28])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 59544023Benzyl 11-(methoxy(methyl)amino)-11-oxoundecylcarbamateHCID 178418332HCID 178418332, compound

Product 1

HCID 59544025Benzyl 11-oxododecylcarbamateYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 20 (1.11 g, 2.94 mmol) in THF (anhydrous, 10 mL) and cooled in an ice bath was added dropwise MeMgCl (3 M solution in diethyl ether, 3.92 mL, 11.75 mmol) over 10 min, and stirring continued at 0° C. for 6 h. The reaction was quenched by the slow addition of methanol (10 mL), and then concentrated under vacuum. The residue was chromatographed (silica gel, a gradient of 0:100 to 18:82 ethyl acetate/hexanes) to afford the desired product 21 (0.78 g, 80% yield) as a white solid: 1H NMR (300 MHz, CDCl3) δ 1.26 (m, 12H), 1.49-1.57 (m, 4H), 2.13 (s, 3H), 2.41 (m, 2H), 3.19 (m, 5H), 5.09 (s, 2H), 7.34 (m, 5H); m/z (ESI) 334 [M+H]+.

Workup

  1. customThe reaction was quenched by the slow addition of methanol (10 mL)
  2. concentrationconcentrated under vacuum
  3. customThe residue was chromatographed (silica gel

Sources & evidence

ORD record
ord-aef4a6c8b67a453da5b8a832f6ea419c
Source dataset
uspto-grants-2012_12
Patent number
US08324218B2

Reaction notes

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