Borane → HCID 21904405, compound

HRID 1839200Notes

Reaction equation

HRID 1839200 reaction equation
[C:1]1([NH:7][C:8]([CH:10]2[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11]2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B>C1COCC1>[C:14]([N:12]1[CH2:13][CH:10]([CH2:8][NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:11]1)([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15]

Participants

4

Reactant 2

HCID 6331BoraneHCID 53646239HCID 53646239, compound

Product 1

HCID 21904405HCID 21904405, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-Boc-Azetidine-3-carboxylic acid phenylamide 47 (650 mg, 2.35 mmol) in 5 mL of dry THF was added slowly to 5 mL of 1.0 M borane in THF while stirring in an ice bath. The mixture was refluxed for 3 hours, then cooled in ice bath and quenched with 5 mL of aqueous HCl (10%), then treated with NaOH (10%) to pH 10. The mixture was extracted with ethyl acetate (3×20 mL). The extracts were combined and washed with brine (2×10 mL), and dried over anhydrous sodium sulfate. After the solvent was removed, the remaining oily residue was passed through a short column (silica gel, ethyl acetate) to afford N-(1-Boc-azetidine-3-ylmethyl)aniline 48 as a colorless oil (520 mg, 84%).

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. temperaturecooled in ice bath
  3. customquenched with 5 mL of aqueous HCl (10%)
  4. additiontreated with NaOH (10%) to pH 10
  5. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  6. washwashed with brine (2×10 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customAfter the solvent was removed

Sources & evidence

ORD record
ord-e59e2da52aa441eea3d0f6f8626fc1c6
Source dataset
uspto-grants-2004_01
Patent number
US06677332B1

Reaction notes

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