Hydrazine hydrate (1:1) → Tert-butyl 3-(2-hydrazinyl-2-oxoethyl)azetidine-1-carboxylate

HRID 1430707Notes

Reaction equation

HRID 1430707 reaction equation
C[O:2][C:3](=O)[CH2:4][CH:5]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6]1.[NH2:17][NH2:18].O>CO>[NH:17]([C:3](=[O:2])[CH2:4][CH:5]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6]1)[NH2:18]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 53249565tert-Butyl 3-(2-methoxy-2-oxoethyl)azetidine-1-carboxylate

Product 1

HCID 67355105Tert-butyl 3-(2-hydrazinyl-2-oxoethyl)azetidine-1-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of tert-butyl 3-(2-methoxy-2-oxoethyl)azetidine-1-carboxylate (25.0 g, 109 mmol) in MeOH (150 mL) was added NH2NH2.H2O (27.3 g, 546 mmol) at rt. The mixture was heated at 65° C. for 12 hrs and then concentrated. The residue was diluted with DCM (400 mL), washed with water (2×) and saturated sodium chloride (2×), dried over Na2SO4, and concentrated to give tert-butyl 3-(2-hydrazinyl-2-oxoethyl)azetidine-1-carboxylate (24.0 g, 96%) as a yellow gum. ESI-MS (EI+, m/z): 252 [M+Na]+.

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with DCM (400 mL)
  3. washwashed with water (2×) and saturated sodium chloride (2×)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9ad34be9b22b403a8855796df170c551
Source dataset
uspto-grants-2015_01
Patent number
US08940897B2

Reaction notes

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