Hydrazine hydrate (1:1) → (R)-O-((1,4-dioxan-2-yl)methyl)hydroxylamine

HRID 656569Notes

Reaction equation

HRID 656569 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][CH2:3][C@@H:2]1[CH2:7][O:8][N:9]1C(=O)C2C(=CC=CC=2)C1=O.O.NN>CO.ClCCl>[O:1]1[CH2:6][CH2:5][O:4][CH2:3][C@@H:2]1[CH2:7][O:8][NH2:9]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57999306(R)-2-((1,4-dioxan-2-yl)methoxy)isoindoline-1,3-dione

Product 1

HCID 57999063(R)-O-((1,4-dioxan-2-yl)methyl)hydroxylamineYield 61.4%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

2L (4.30 g, 12.4 mmol) was dissolved in 90 mL of methanol/dichloromethane 1/9 ratio. Hydrazine hydrate (1.67 mL, 22.4 mmol) was added and the reaction was stirred at room temperature for 2 h at which time the deprotection was done. The precipitate byproduct was filtered, and the filtrate was concentrated down to an oil and then purified by flash column chromatography, using chloroform/methanol 99/1 ratio to yield (R)—O-((1,4-dioxan-2-yl)methyl)hydroxylamine (2M, 0.915 g, 61.4% yield over 2 steps). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 3.41 (t, J=10.86 Hz, 1H) 3.57-3.71 (m, 4H) 3.71-3.82 (m, 3H) 3.83-3.92 (m, 1H) 5.55 (br. s., 2H).

Workup

  1. filtrationThe precipitate byproduct was filtered
  2. concentrationthe filtrate was concentrated down to an oil
  3. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-d39124c5425d4392866291c9a386a83f
Source dataset
uspto-grants-2011_12
Patent number
US08071766B2

Reaction notes

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