Di-tert-butyl dicarbonate → rac-tert-Butyl (2-cyanopentan-2-yl)carbamate 2-methylpropan-2-ol

HRID 1486316Notes

Reaction equation

HRID 1486316 reaction equation
C(O[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=O.[NH2:16][C:17]([CH3:23])([CH2:20][CH2:21][CH3:22])[C:18]#[N:19]>ClCCl>[C:18]([C:17]([NH:16][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])([CH2:20][CH2:21][CH3:22])[CH3:23])#[N:19].[CH3:5][C:4]([OH:3])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 208880Pentanenitrile, 2-amino-2-methyl-

Product 1

HCID 131736783rac-tert-Butyl (2-cyanopentan-2-yl)carbamate 2-methylpropan-2-olYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

64.21 g (294.18 mmol) of di-tert-butyl dicarbonate were initially charged in a round-bottom flask, and 30 g (267.44 mmol) of rac-2-amino-2-methylpentanenitrile were added very gradually at RT (internal thermometer, maximum temperature 30° C.), and stirring of the mixture was continued at room temperature overnight. The reaction mixture was admixed with dichloromethane and washed twice with 1 N sodium hydroxide solution. The organic phase was dried over sodium sulphate, filtered and concentrated (at bath temperature 30° C.). 76.33 g (quantitative yield) of the target compound were obtained.

Workup

  1. washwashed twice with 1 N sodium hydroxide solution
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated (at bath temperature 30° C.)

Sources & evidence

ORD record
ord-0160c8269e2641ceae4cb0fac7081b10
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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