Boron trifluoride etherate → N-Cbz-2-amino 1-[di-(t-butyl)methoxy]propane

HRID 1906996Notes

Reaction equation

HRID 1906996 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].[C:15]([CH:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[OH:20])([CH3:18])([CH3:17])[CH3:16].B(F)(F)F.CCOCC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([NH:11][CH:12]([CH3:14])[CH2:13][O:20][CH:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:15]([CH3:18])([CH3:17])[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 1397902,2,4,4-Tetramethylpentan-3-olHCID 516892Sodium BicarbonateHCID 21895246Benzyl 2-methylaziridine-1-carboxylate

Product 1

HCID 20201216N-Cbz-2-amino 1-[di-(t-butyl)methoxy]propane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Cbz-2-Methyl aziridine and di-t-butylmethanol 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-2-amino 1-[di-(t-butyl)methoxy]propane.

Workup

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

Sources & evidence

ORD record
ord-a14d7a38c3b94408bc7f0c7cc52d79e9
Source dataset
uspto-grants-1987_03
Patent number
US04654439

Reaction notes

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