Methylhydrazine → (R)-O-((2,2-Dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamine

HRID 2218458Notes

Reaction equation

HRID 2218458 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][C@@H:5]([CH2:7][OH:8])[CH2:4][O:3]1.[CH3:10][C:11]1([CH3:29])[O:15][C@@H:14]([CH2:16][O:17][N:18]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:13][O:12]1.CNN>ClCCl>[CH3:1][C:2]1([CH3:9])[O:6][C@@H:5]([CH2:7][OH:8])[CH2:4][O:3]1.[CH3:10][C:11]1([CH3:29])[O:15][C@@H:14]([CH2:16][O:17][NH2:18])[CH2:13][O:12]1

Participants

6

Reactant 3

HCID 6061MethylhydrazineHCID 736057(+)-SolketalHCID 14814200HCID 14814200, compound

Product 2

HCID 736057(+)-SolketalHCID 11298047(R)-O-((2,2-Dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamineYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of (S)- or (R)-2-(2,2-Dimethyl-[1,3]dioxolan-4-ylmethoxy)-isoindole-1,3-dione (74.9 g, 0.27 mol) in dichloromethane (480 mL) at 3-5° C. was added methylhydrazine (15.8 mL, 0.29 mole) dropwise. The color of the suspension turned from yellow to white. The cooling bath was removed and the mixture was stirred for 2 hrs at ambient temperature. The resulting suspension was concentrated on a rotary evaporator. To the white solid was added ether (0.5 L) and the resulting mixture was stirred for 1.5 h at ambient temperature. The white precipitate was filtered and washed with ether (0.2 L). The filtrate was concentrated on rotary evaporator to give (S)- or (R)-O-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-hydroxylamine (39.0 g, 98.3%): 1H NMR (CDCl3): δ 1.35 (s, 3H), 1.42 (s, 3H), 3.73 (m, 3H), 4.05 (m, 1H), 4.33 (m, 1H), 5.39 (m, 2H); MS (APCI+)=148.1 (M++1)

Workup

  1. customThe cooling bath was removed
  2. concentrationThe resulting suspension was concentrated on a rotary evaporator
  3. additionTo the white solid was added ether (0.5 L)
  4. stirringthe resulting mixture was stirred for 1.5 h at ambient temperature
  5. filtrationThe white precipitate was filtered
  6. washwashed with ether (0.2 L)
  7. concentrationThe filtrate was concentrated on rotary evaporator

Sources & evidence

ORD record
ord-a030f556b6cf4602b06d01524838f057
Source dataset
uspto-grants-2008_08
Patent number
US07411001B2

Reaction notes

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