Water → 3-(tert-Butyldimethylsiloxymethyl)benzylamine

HRID 585517Notes

Reaction equation

HRID 585517 reaction equation
NN.[Si:3]([O:10][CH2:11][C:12]1[CH:13]=[C:14]([CH:27]=[CH:28][CH:29]=1)[CH2:15][N:16]1C(=O)C2C(=CC=CC=2)C1=O)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].O.ClCCl>C(O)C>[Si:3]([O:10][CH2:11][C:12]1[CH:13]=[C:14]([CH:27]=[CH:28][CH:29]=1)[CH2:15][NH2:16])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 9321HydrazineHCID 208241182-[3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)benzyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 220499793-(tert-Butyldimethylsiloxymethyl)benzylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

At room temperature, a hydrazine solution (35% strength in water, 0.6 ml, 6.6 mmol) is added to a solution of 2-[3-({[tert-butyl(dimethyl)silyl]oxy}methyl)benzyl]-1H-isoindole-1,3(2H)-dione (1.7 g, 4.4 mmol) in ethanol (44 ml), the mixture is stirred at room temperature for 15 h and water is added. After addition of dichloromethane and phase separation, the aqueous phase is extracted with dichloromethane. The combined organic phases are dried (sodium sulfate), filtered and concentrated under reduced pressure. The desired product is used without further purification for the next reaction.

Workup

  1. extractionthe aqueous phase is extracted with dichloromethane
  2. dry with materialThe combined organic phases are dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe desired product is used without further purification for the next reaction

Sources & evidence

ORD record
ord-c6e8cbf37021488c80ea5c5323bc66ea
Source dataset
uspto-grants-2005_08
Patent number
US06933295B2

Reaction notes

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