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

HRID 2218447Notes

Reaction equation

HRID 2218447 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-58efa8e4e80d432fbb538fdd44eb53d8
Source dataset
uspto-grants-2008_08
Patent number
US07411001B2

Reaction notes

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