Borane;tetrahydrofuran → HCID 67107599, compound

HRID 2177849Notes

Reaction equation

HRID 2177849 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[C:4]([CH:6]1[CH2:9][CH2:8][N:7]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=O)[CH3:2].B.C1COCC1>C1COCC1>[CH2:1]([N:3]([CH2:4][CH:6]1[CH2:9][CH2:8][N:7]1[C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH2:17][CH3:18])[CH3:2]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 67107644HCID 67107644, compound

Product 1

HCID 67107599HCID 67107599, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of t-butyl 2-diethylcarbamoylazetidine-1-carboxylate (0.614 g) in THF (15 ml) was cooled in an ice/water bath and borane/THF complex (1M in THF, 7.68 ml) was added dropwise over 15 minutes. The mixture was then warmed to room temperature and stirred for a further 18 hours. The mixture was evaporated to dryness and ethanol and water (9:1, 20 ml) was added. The reaction mixture was then heated to reflux for 3 hours. After cooling, it was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of DCM:methanol:acetic acid:water with a gradient of 350:20:3:2 to 120:15:3:2 to give t-butyl 2-diethylaminomethylazetidine-1-carboxylate (0.47 g) as a yellow oil.

Workup

  1. customThe mixture was evaporated to dryness and ethanol and water (9:1, 20 ml)
  2. additionwas added
  3. temperatureThe reaction mixture was then heated
  4. temperatureto reflux for 3 hours
  5. temperatureAfter cooling
  6. customit was evaporated to dryness
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of DCM

Sources & evidence

ORD record
ord-98966e28cc4047a8b3555ee5e04a1b2c
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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