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

HRID 746187Notes

Reaction equation

HRID 746187 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 drid over MgSO4 and evaporated to yield N-Cbz-2-amino 1-[di-(t-butyl)methoxy]propane.

Workup

  1. extractionare extracted with ethyl acetate
  2. customevaporated

Sources & evidence

ORD record
ord-a314b7ccc7ef4bcc8f231c992f29236a
Source dataset
uspto-grants-1986_07
Patent number
US04603011

Reaction notes

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