Trifluoroacetic acid → HCID 21060031, compound

HRID 921946Notes

Reaction equation

HRID 921946 reaction equation
Cl.[CH2:2]1[C:6]2([CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]2)[CH2:5][CH2:4][NH:3]1.[CH3:19][C:20](OC(C)=O)=[O:21].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:2]1[C:6]2([CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)[CH2:5][CH2:4][N:3]1[C:20](=[O:21])[CH3:19]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7918Acetic AnhydrideHCID 66833979tert-Butyl 2,8-diazaspiro[4.5]decane-8-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 21060031HCID 21060031, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of tert-butyl 2,8-diazaspiro[4.5]decane-8-carboxylate hydrochloride (400 mg, 1.445 mmol) in DCM (5 mL) was treated with TEA (0.604 mL, 4.34 mmol), followed by Ac2O (0.164 mL, 1.734 mmol), stirred at room temperature for 2 h. To this reaction mixture was added TFA (2.115 mL, 27.5 mmol) and stirred at room temperature for h. Concentrated under reduced pressure to obtain crude material which purified by SCX cartridge, loading with MeOH, washed with additional MeOH. Product was recovered eluting with 2M NH3 in MeOH. Solvent evaporation gave 1-(2,8-diazaspiro[4.5]decan-2-yl)ethanone (165 mg)

Workup

  1. stirringstirred at room temperature for h
  2. concentrationConcentrated under reduced pressure
  3. customto obtain crude material which
  4. custompurified by SCX cartridge
  5. washwashed with additional MeOH
  6. customProduct was recovered
  7. washeluting with 2M NH3 in MeOH
  8. customSolvent evaporation

Sources & evidence

ORD record
ord-1d15aa6bae0344c7ba5e166c51504ed8
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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