Methylhydrazine → O-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-hydroxylamine

HRID 1062270Notes

Reaction equation

HRID 1062270 reaction equation
[C:1]([Si:5]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[O:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][N:12]1C(=O)C2C(=CC=CC=2)C1=O)([CH3:4])([CH3:3])[CH3:2].CNN>ClCCl>[C:1]([Si:5]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[O:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][NH2:12])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 222863132-[4-(Tert-butyl-diphenyl-silanyloxy)-butoxy]-isoindole-1,3-dione

Product 1

HCID 22286549O-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-hydroxylamineYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-[4-(tert-butyl-diphenyl-silanyloxy)-butoxy]-isoindole-1,3-dione (11.1 g, 23.4 mmol) in dichloromethane (100 ml) was treated with methylhydrazine. The reaction mixture was stirred overnight and was filtered. The filtrate was concentrated and purified by column chromatography [hexane/ethyl acetate (3.5/1)] to afford O-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-hydroxylamine (7.2 g, 90% yield) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 7.62-7.66(4H, m), 7.33-7.42 (6H, m), 3.64-3.68(4H), 1.54-1.70 (4H, m), 1.02 (9H, s); MS (APCI+)=344.2.

Workup

  1. filtrationwas filtered
  2. concentrationThe filtrate was concentrated
  3. custompurified by column chromatography [hexane/ethyl acetate (3.5/1)]

Sources & evidence

ORD record
ord-da0344b6abd3459092ea48a3927d7f8e
Source dataset
uspto-grants-2005_11
Patent number
US06960614B2

Reaction notes

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