Methyl 2-(allyl(benzyl)amino)acetate → HCID 86729460, compound

HRID 712389Notes

Reaction equation

HRID 712389 reaction equation
[CH2:1]([N:4]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5][C:6](OC)=[O:7])[CH:2]=[CH2:3].C1([Mg]Cl)CCCC1>C1COCC1>[CH2:10]([N:4]1[CH2:1][C@H:2]2[C@:6]([OH:7])([CH2:3]2)[CH2:5]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 10798914Methyl 2-(allyl(benzyl)amino)acetateHCID 178478989HCID 178478989, compound

Product 1

HCID 86729460HCID 86729460, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(allyl(benzyl)amino)acetate (0.76 g, 3.5 mmol, 1.0 eq) in anhydrous THF (50 mL) at 20° C. under N2 was added ClTi(OiPr)3 (3.50 mL, 3.50 mmol, 1.0 eq) followed by cyclopentylmagnesium chloride (7.80 mL, 15.6 mmol, 4.5 eq) dropwise via a syringe pump over 4 h. The reaction mixture was quenched with a little of water and extracted with EtOAc (20 mL×3). The combined organic phases were washed with water followed by brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (1:1 (v/v) PE/EtOAc) to afford the title compound as colorless oil (0.48 g, 73%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 190.2 (M+1); 1H NMR (400 MHz, CDCl3) δ: 0.83 (2H, m), 1.09 (1H, t, J=4.8 Hz), 1.36 (1H, m), 2.57 (2H, m), 2.72 (1H, d, J=8.8 Hz), 3.05 (1H, d, J=8.4 Hz), 3.60 (2H, s), 7.25 (5H, m) ppm.

Workup

  1. customThe reaction mixture was quenched with a little of water
  2. extractionextracted with EtOAc (20 mL×3)
  3. washThe combined organic phases were washed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (1:1 (v/v) PE/EtOAc)

Sources & evidence

ORD record
ord-9e03f4cf5a7c4ca795b738b8952f1261
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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