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

HRID 979013Notes

Reaction equation

HRID 979013 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].[C:16]([CH:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[OH:21])([CH3:19])([CH3:18])[CH3:17].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:21][CH:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:16]([CH3:19])([CH3:18])[CH3:17])([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 13930700HCID 13930700, compound

Product 1

HCID 20201229N-Cbz-2-amino-2-methyl-1-[di-(t-butyl)methoxy]propane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Cbz-2,2-Dimethyl 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 extracted with ethyl acetate. The organic layer is dried over MgSO4 and evaporated to yield N-Cbz-2-amino-2-methyl-1-[di-(t-butyl)methoxy]propane.

Workup

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

Sources & evidence

ORD record
ord-0b19297fe0434dada8ac65adedb4365e
Source dataset
uspto-grants-1987_05
Patent number
US04666729

Reaction notes

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