Boron trifluoride etherate → N-Cbz-1-(2-amino-2-methylpropoxy)-2,2,5,5-tetramethylcyclopentane

HRID 255463Notes

Reaction equation

HRID 255463 reaction equation
[C:1]([N:11]1[CH2:13][C:12]1([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH3:16][C:17]1([CH3:25])[CH2:21][CH2:20][C:19]([CH3:23])([CH3:22])[CH:18]1[OH:24].B(F)(F)F.CCOCC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([NH:11][C:12]([CH3:14])([CH3:15])[CH2:13][O:24][CH:18]1[C:19]([CH3:23])([CH3:22])[CH2:20][CH2:21][C:17]1([CH3:25])[CH3:16])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 5516962,2,5,5-Tetramethylcyclopentan-1-olHCID 13930700N-Cbz-2,2-dimethylaziridine

Product 1

HCID 20165753N-Cbz-1-(2-amino-2-methylpropoxy)-2,2,5,5-tetramethylcyclopentane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Cbz-2,2-dimethyl aziridine and 2,2,5,5-tetramethyl-1-cyclopentanol are dissolved in CH2Cl2 at 0° C. under argon. Boron trifluoride etherate is added and the flask is stirred overnight. The contents are poured into saturated NaHCO3 and extracted with ethyl acetate. The organic layer is dried over MgSO4 and evaporated to yield N-Cbz-1-(2-amino-2-methylpropoxy)-2,2,5,5-tetramethylcyclopentane.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer is dried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-4a2da85c3442415396a9e6d20250e482
Source dataset
uspto-grants-1987_10
Patent number
US04698231

Reaction notes

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