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

HRID 369828Notes

Reaction equation

HRID 369828 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-9b92180d005744b8b89884ee3de464e9
Source dataset
uspto-grants-2000_10
Patent number
US06140326

Reaction notes

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