Hydrazine hydrate (1:1) → 8-t-Butyl-2-aminomethyl-1,4-dioxaspiro(4,5)decane

HRID 2211124Notes

Reaction equation

HRID 2211124 reaction equation
[C:1]([CH:5]1[CH2:26][CH2:25][C:8]2([O:12][CH:11]([CH2:13][N:14]3C(=O)C4=CC=CC=C4C3=O)[CH2:10][O:9]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].O.NN>C(O)C>[C:1]([CH:5]1[CH2:26][CH2:25][C:8]2([O:12][CH:11]([CH2:13][NH2:14])[CH2:10][O:9]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 199636648-t-Butyl-2-(phthalimidomethyl)-1,4-dioxaspiro(4,5)decane

Product 1

HCID 199636658-t-Butyl-2-aminomethyl-1,4-dioxaspiro(4,5)decaneYield 90.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a warm (50° C.) solution of 8-t-butyl-2-(phthalimidomethyl)-1,4-dioxaspiro (4,5)decane (12.5 g, 35 mmol) in ethanol (100 ml) was 25 added hydrazine hydrate (3.6 g, 72 mmol). The reaction mixture was kept at 50° C. for 1 hour. Light petroleum 200 ml was added and insoluble material was filtered off. The solvent was evaporated in vacuo. The residue was dissolved in toluene (100 ml) washed with brine (100 ml) and dried (MgSO4). Evaporation of the solvent yielded the title compound as a yellow oil (7.2 g). GC analysis indicated the compound as existing as a mixture of two diastereoisomers (cis, cis and cis, trans) in a ratio of 48:52. The NMR spectra are in agreement with the assigned structure.

Workup

  1. filtrationinsoluble material was filtered off
  2. customThe solvent was evaporated in vacuo
  3. dissolutionThe residue was dissolved in toluene (100 ml)
  4. washwashed with brine (100 ml)
  5. dry with materialdried (MgSO4)
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f89ff1c7717e47eebc530490f9446f49
Source dataset
uspto-grants-1995_10
Patent number
US05462944

Reaction notes

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