Triethylamine → Tert-butyl 3-(dimethylamino)azetidine-1-carboxylate

HRID 1842693Notes

Reaction equation

HRID 1842693 reaction equation
[CH3:1][N:2]([CH3:7])[CH:3]1[CH2:6][NH:5][CH2:4]1.C(N(CC)CC)C.[C:15](=O)([O:21]C(OC(C)(C)C)=O)[O:16][C:17]([CH3:20])([CH3:19])[CH3:18]>C(Cl)Cl>[CH3:1][N:2]([CH3:7])[CH:3]1[CH2:6][N:5]([C:15]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:21])[CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 10351656N,N-dimethylazetidin-3-amine2×

Product 1

HCID 23145930Tert-butyl 3-(dimethylamino)azetidine-1-carboxylateYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N,N-dimethylazetidin-3-amine (Intermediate 28, 100 g, 1.0 mol) and triethylamine (487 mL, 3.5 mol) in CH2Cl2 (500 mL) was added tert-butyl (2-methylpropan-2-yl)oxycarbonyl carbonate (326 g, 1.5 mol) at 0° C. The mixture was then stirred at r.t. for 5 h. The mixture was then washed with water (4×500 mL) and the organic solution were dried (Na2SO4) and concentrated in vacuo. Purification by FCC gave the title compound (62 g, 31%).

Workup

  1. washThe mixture was then washed with water (4×500 mL)
  2. dry with materialthe organic solution were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customPurification by FCC

Sources & evidence

ORD record
ord-610069430f80400e8967d979973b4494
Source dataset
uspto-grants-2015_02
Patent number
US08946235B2

Reaction notes

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