Methylhydrazine → O-(3-((tert-Butyldimethylsilyl)oxy)propyl)hydroxylamine

HRID 1062267Notes

Reaction equation

HRID 1062267 reaction equation
[C:1]([Si:5]([CH3:23])([CH3:22])[O:6][CH2:7][CH2:8][CH2:9][O:10][N:11]1C(=O)C2C(=CC=CC=2)C1=O)([CH3:4])([CH3:3])[CH3:2].CNN>ClCCl>[C:1]([Si:5]([CH3:22])([CH3:23])[O:6][CH2:7][CH2:8][CH2:9][O:10][NH2:11])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 22286311HCID 22286311, compound

Product 1

HCID 22286275O-(3-((tert-Butyldimethylsilyl)oxy)propyl)hydroxylamineYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-[3-(tert-butyl-dimethyl-silanyloxy)-propoxy]-isoindole-1,3-dione (26.3 g, 78.3 mmol) in dichloromethane (120 mL) was cooled to 0° C. and treated with methylhydrazine (16.1 g, 78.3 mmol). The reaction mixture was stirred for 30 min at 0° C. and filtered. The filtrate was concentrated under reduced pressure, redissolved in ether, and refrigerated (4° C.) overnight. The resultant crytalline material was removed by filtration and the filtrate was concentrated under reduced pressure to afford O-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-hydroxylamine (15.95 g, 99% yield) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 4.69 (br s,2H), 3.74 (t, J=6.3 Hz, 2H), 3.67 (t, J=6.3 Hz, 2H), 1.78 (quintet, J=6.3 Hz, 2H), 0.88 (s, 9H), 0.00 (s, 6H); MS (APCI+)=206.1. Anal. Calcd./Found for C9H23NO2Si: C, 52.64/52.22; H, 11.29/10.94; N, 6.82/6.46.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. dissolutionredissolved in ether
  4. customrefrigerated (4° C.) overnight
  5. customThe resultant crytalline material was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8927be7c9542457499d72dd2d7d931fb
Source dataset
uspto-grants-2005_11
Patent number
US06960614B2

Reaction notes

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