Ammonia → tert-Butyl (aminooxy)acetate

HRID 328450Notes

Reaction equation

HRID 328450 reaction equation
[C:1]([O:5][C:6]([CH2:8][O:9][N:10]1C(=O)C2=CC=CC=C2C1=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.NN.N.CCOCC>C(Cl)Cl.CO>[C:1]([O:5][C:6]([CH2:8][O:9][NH2:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 3283Diethyl EtherHCID 24654Hydrazine hydrate (1:1)HCID 12919120Tert-butyl 2-(1,3-dioxoisoindolin-2-yloxy)acetate

Product 1

HCID 12919121tert-Butyl (aminooxy)acetate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of N-t-butoxycarbonylmethoxyphthalimide (21g) in methylene chloride (250ml) was treated with 100% hydrazine hydrate (7.6ml) in methanol (15ml), and the mixture was stirred for 1.5 hr. 5N-Ammonia solution was added to dissolve the precipitated solid. The organic layer was separated, and the aqueous layer was further extracted with methylene chloride. The combined extracts were washed with water, dried, and evaporated to give a pale-yellow solid. To this was added ether, the mixture was filtered, and the filtrate evaporated to give t-butoxycarbonylmethoxyamine as a pale yellow liquid, (8.88g, 80%); νmax. (Nujol) includes 3330, 3260 cm.-1 (NH2), 1742 cm.-1 (-COOBut); τ values (DMSO-d6) are 3.75 (-NH2), 5.96 (CH2) 8.55 (But).

Workup

  1. dissolutionto dissolve the precipitated solid
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was further extracted with methylene chloride
  4. washThe combined extracts were washed with water
  5. customdried
  6. customevaporated
  7. customto give a pale-yellow solid
  8. filtrationthe mixture was filtered
  9. customthe filtrate evaporated

Sources & evidence

ORD record
ord-95b5638c268f48f3bfc69b454ad43d29
Source dataset
uspto-grants-1977_04
Patent number
US04017515

Reaction notes

Loading…