tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamate → HCID 18534818, compound

HRID 412003Notes

Reaction equation

HRID 412003 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:13])([CH3:12])[CH:10]=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:14][CH:15]([SiH3])[CH:16]=C(C)C>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C:9]([CH3:13])([CH3:12])[CH:10]([OH:11])[CH2:16][CH:15]=[CH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14578674tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamateHCID 131722132HCID 131722132, compound

Product 1

HCID 18534818HCID 18534818, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of the product of step b (20 mmol, 3.74 g) in 20 ml of CH2Cl2 at −78° C., 22 ml of a solution 1 M of TiCl4 in CH2Cl2 is added. After 10 min, trimethyallylsilane (22 mmol, 3.5 ml) in 20 ml of CH2Cl2 is added. After one hour the reaction is quenched with water. The organic layer is separated and extracted with CH2Cl2 (3×25 ml). The solution is anhydrified (Na2SO4) and after concentration 1.14 g of product is obtained.

Workup

  1. customAfter one hour the reaction is quenched with water
  2. customThe organic layer is separated
  3. extractionextracted with CH2Cl2 (3×25 ml)
  4. customafter concentration 1.14 g of product is obtained

Sources & evidence

ORD record
ord-61ab3b8673a044b08d2c32118baef9da
Source dataset
uspto-grants-2003_05
Patent number
US06562815B1

Reaction notes

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