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

HRID 1731676Notes

Reaction equation

HRID 1731676 reaction equation
[C:1]([N:11]1[CH2:13][CH:12]1[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH3:15][C:16]1([CH3:24])[CH2:20][CH2:19][C:18]([CH3:22])([CH3:21])[CH:17]1[OH:23].B(F)(F)F.CCOCC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([NH:11][CH:12]([CH3:14])[CH2:13][O:23][CH:17]1[C:18]([CH3:22])([CH3:21])[CH2:19][CH2:20][C:16]1([CH3:24])[CH3:15])([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 21895246Benzyl 2-methylaziridine-1-carboxylate

Product 1

HCID 20165723N-Cbz-1-(2-aminopropoxy)-2,2,5,5-tetramethylcyclopentane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Cbz-2-Methyl 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 are extracted with ethyl acetate. The organic layer is dried over MgSO4 and evaporated to yield N-Cbz-1-(2-aminopropoxy)-2,2,5,5-tetramethylcyclopentane.

Workup

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

Sources & evidence

ORD record
ord-325613c252f74051a1454e7627157224
Source dataset
uspto-grants-1986_11
Patent number
US04622418

Reaction notes

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