Sodium Hydroxide → Bicyclo(3.1.1)heptane-3-methanamine, 2,6,6-trimethyl-

HRID 1388578Notes

Reaction equation

HRID 1388578 reaction equation
Cl.[NH2:2][CH2:3][CH:4]1[CH2:9][CH:8]2[CH2:10][CH:6]([C:7]2([CH3:12])[CH3:11])[CH:5]1[CH3:13].[OH-].[Na+]>C(OCC)(=O)C>[NH2:2][CH2:3][CH:4]1[CH2:9][CH:8]2[CH2:10][CH:6]([C:7]2([CH3:12])[CH3:11])[CH:5]1[CH3:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 106575Bicyclo[3.1.1]heptane-3-methanamine, 2,6,6-trimethyl-, hydrochloride (1:1)

Product 1

HCID 106576Bicyclo(3.1.1)heptane-3-methanamine, 2,6,6-trimethyl-

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(-)-3-Aminomethylpinane HCl, 9.5 g (46.6 mmole), ethyl acetate (186 ml) and 1 N NaOH (93 ml) were stirred vigorously for 10 minutes. The organic layer was separated, washed 1×93 ml H2O, dried (MgSO4) and stripped to yield (-)-3-aminomethylpinane free base as an oil, 7.75 g (99%) [alpha]D25 =-54.85° (c=1 in methanol), which was then dissolved in 20 ml methanol.

Workup

  1. customThe organic layer was separated
  2. washwashed 1×93 ml H2O
  3. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-11e54d39c18b42acb6e5a7437b3ed711
Source dataset
uspto-grants-1984_02
Patent number
US04431828

Reaction notes

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