HCID 86729462, compound → (1R,5S)-3-benzyl-N,N-dimethyl-3-azabicyclo[3.1.0]hexan-1-amine

HRID 712392Notes

Reaction equation

HRID 712392 reaction equation
[CH2:1]([N:4]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:5][C:6]([N:8]([CH3:10])[CH3:9])=O)[CH:2]=[CH2:3].C([Mg]Br)(C)C>C1COCC1>[CH2:11]([N:4]1[CH2:1][C@H:2]2[C@:6]([N:8]([CH3:10])[CH3:9])([CH2:3]2)[CH2:5]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 86729462HCID 86729462, compoundHCID 178418365HCID 178418365, compound

Product 1

HCID 86729463(1R,5S)-3-benzyl-N,N-dimethyl-3-azabicyclo[3.1.0]hexan-1-amineYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(allyl(benzyl)amino)-N,N-dimethylacetamide (0.57 g, 2.45 mmol, 1.0 eq) in anhydrous THF (25 mL) at room temperature under N2 was added ClTi(OiPr)3 (2.45 mL, 2.45 mmol, 1.0 eq) followed by i-PrMgBr (1.0M in ether, 11.0 mL, 11.0 mmol, 4.5 eq) via a syringe pump over 1 h. The reaction mixture was stirred for another 2 h, and then quenched with a small amount of water. The mixture was extracted with EtOAc (20 mL×3), the combined organic phases were washed with water and brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by a silica gel column chromatography (30:1 (v/v) CH2Cl2/CH3OH) to give the title compound as colorless oil (0.33 g, 63%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 217.35 (M+1).

Workup

  1. customquenched with a small amount of water
  2. extractionThe mixture was extracted with EtOAc (20 mL×3)
  3. washthe combined organic phases were washed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by a silica gel column chromatography (30:1 (v/v) CH2Cl2/CH3OH)

Sources & evidence

ORD record
ord-945ddda7dd784b8ebfad6853beffe4ca
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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