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

HRID 1973158Notes

Reaction equation

HRID 1973158 reaction equation
[H][H].[CH:3]([CH:5]1[CH2:10][CH:9]2[CH2:11][CH:7]([C:8]2([CH3:13])[CH3:12])[CH:6]1[CH3:14])=O.[NH3:15]>C(O)C.[Co]>[NH2:15][CH2:3][CH:5]1[CH2:10][CH:9]2[CH2:11][CH:7]([C:8]2([CH3:13])[CH3:12])[CH:6]1[CH3:14]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 108415Bicyclo[3.1.1]heptane-3-carboxaldehyde, 2,6,6-trimethyl-HCID 178418361HCID 178418361, compound2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 702EthanolSolvent

Procedure

150 g of Raney cobalt, suspended in 1,000 ml of ethanol and 3.5 kg of ammonia, are heated to 80° C in a stirred autoclave, and hydrogen is then introduced until the total pressure is 150 bars. 2,020 g of (-)-3-formylpinane are pumped in over 6 hours. The pressure is kept constant by replenishing with hydrogen. After completion of the reaction, the autoclave is allowed to cool and the pressure is then released. The reaction product, weighing 3,450 g, is worked up by fractional distillation, giving 1,450 g of structurally pure (-)-3-aminomethylpinane, which boils at 100° C at 11 mm Hg and has an optical rotation of [α]D23 = -32.6° (pure).

Workup

  1. additionis then introduced until the total pressure
  2. customare pumped in over 6 hours
  3. customAfter completion of the reaction
  4. temperatureto cool
  5. distillationis worked up by fractional distillation

Sources & evidence

ORD record
ord-4d0b74668ff3423daa9726efc19886d1
Source dataset
uspto-grants-1976_12
Patent number
US03996246

Reaction notes

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