Methylhydrazine → (S)-O-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamine

HRID 1089275Notes

Reaction equation

HRID 1089275 reaction equation
[CH3:1][C:2]1([CH3:20])[O:6][C@H:5]([CH2:7][O:8][N:9]2C(=O)C3=CC=CC=C3C2=O)[CH2:4][O:3]1.CNN>ClCCl>[CH3:1][C:2]1([CH3:20])[O:6][C@H:5]([CH2:7][O:8][NH2:9])[CH2:4][O:3]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 14814201(S)-N-(2,2-Dimethyl-1,3-dioxolan-4-ylmethoxy)phthalimide

Product 1

HCID 14814202(S)-O-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamineYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of (S)-N-(2,2-Dimethyl-1,3-dioxolan-4-ylmethoxy)phthalimide (10 g, 36 mmol), and N-methylhydrazine (3.32 g, 72 mmol) in dichloromethane (150 ml) was stirred at 25° C. for 2 h. The reaction was filtered, evaporated to dryness and the residue suspended in ether. The suspension was filtered and evaporated and the residue chromatographed in ethyl acetate affording (S)-2,2-Dimethyl-1,3-dioxolan-4-ylmethoxyamine (4.8 g, 91%) as a clear liquid [α]D25 -2.4° (0.49 in MeOH); υmax (film) 3550, 3300 and 1600 cm-1 ; δH (CDCl3)1.38(3H,S,CH3), 1.44(3H,S,CH3), 3.71 (3H,m,CH2ON+1H of CH2OCMe2), 4.05(1H,q,J6.3,8.2 Hz,1H of CH2OCMe2), 4.35(1H,m,CH) and 5.57(2H,br.s, D2O exchangeable, NH2); m/z 132 (M+ -CH3, 24%). Found: C, 48.76; H, 9.00; N, 9.56% C6H13NO3 requires C, 48.96; H, 8.90; N, 9.52%

Workup

  1. filtrationThe reaction was filtered
  2. customevaporated to dryness
  3. filtrationThe suspension was filtered
  4. customevaporated
  5. customthe residue chromatographed in ethyl acetate

Sources & evidence

ORD record
ord-24eaa82e582f4e4993601483c10fbef4
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

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