Silane, (chloromethyl)dimethyl- → HCID 18401194, compound

HRID 1019358Notes

Reaction equation

HRID 1019358 reaction equation
[CH2:1]([NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=[CH2:3].[Cl:12][CH2:13][SiH:14]([CH3:16])[CH3:15]>C1(C)C=CC=CC=1>[C:5]([NH:4][CH2:1][CH2:2][CH2:3][Si:14]([CH2:13][Cl:12])([CH3:16])[CH3:15])([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:11]

Participants

4

Reactant 2

HCID 76597Silane, (chloromethyl)dimethyl-HCID 4067274tert-butyl N-(prop-2-en-1-yl)carbamate

Product 1

HCID 18401194HCID 18401194, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
70 °C

Procedure

A 250 mL 3-necked round bottom flask equipped with reflux condenser nitrogen inlet, thermometer heating mantle, pressure equalizing addition funnel and magnetic stirrer was charged with 14.36 g (91.3 mmol) of t-butyl N-allylcarbamate and 150 mL of toluene. The olefin and solvent were stirred and heated to about 70° C., then 10 microliters of Karstedt's catalyst (5% Pt solution, about 30 ppm Pt based on olefin) was added. A solution containing 12 g (110.5 mmol) of chloromethyldimethylsilane in 20 mL toluene was added cautiously over about 30 minutes at a rate sufficient to maintain the reaction temperature between about 80 and about 100° C. After addition was completed, the temperature was stirred and heated at about 85° for about 1 hour. GC-MS indicated complete reaction of the olefin to form the silylated compound, N-Boc-3-aminopropylchloromethyldimethylsilane. The solution was transferred to a 500 ml single neck round bottom flask and the solvent and excess silane were stripped via rotary evaporation to yield 25 g of crude product (quantitative yield based on olefin).

Workup

  1. customA 250 mL 3-necked round bottom flask equipped
  2. temperaturewith reflux condenser nitrogen inlet
  3. additionaddition funnel and magnetic stirrer
  4. additionwas added cautiously over about 30 minutes at a rate sufficient
  5. temperatureto maintain the reaction temperature between about 80 and about 100° C
  6. additionAfter addition
  7. temperatureheated at about 85° for about 1 hour

Sources & evidence

ORD record
ord-ec159a51058d49f7b4f5485d438588d7
Source dataset
uspto-grants-2002_11
Patent number
US06486364B2

Reaction notes

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