Hydrochloric Acid → 8-(Propan-2-yl)-8-azabicyclo[3.2.1]octan-3-one

HRID 1533096Notes

Reaction equation

HRID 1533096 reaction equation
CO[CH:3]1[CH2:7][CH2:6][CH:5](OC)[O:4]1.[CH:10]([NH:13][CH:14]([CH3:16])[CH3:15])([CH3:12])[CH3:11].Cl.C(C(O)=O)C(CC(O)=O)=O.C([O-])(=O)C.[Na+]>Cl.O>[CH:10]([N:13]1[CH:6]2[CH2:5][CH2:16][CH:14]1[CH2:15][C:3](=[O:4])[CH2:7]2)([CH3:12])[CH3:11]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 68328Acetonedicarboxylic acid2×HCID 790982,5-DimethoxytetrahydrofuranHCID 517045Sodium Acetate2×

Product 1

HCID 1030098-(Propan-2-yl)-8-azabicyclo[3.2.1]octan-3-oneYield 27.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent2×

Procedure

2M Hydrochloric acid (8 drops) was added to a stirred solution of 2,5-dimethoxytetrahydrofuran (16.5 g) in water (70 ml). After 15 minutes a mixture of diisopropylamine (7.38 g) and 2M hydrochloric acid (40 ml) was added to the reaction followed by acetonedicarboxylic acid (18.25 g) and sodium acetate (10.0 g) in water (100 ml). After 3 days 1,3-acetonedicarboxylic acid (6.0 g) and sodium acetate (3.0 g) were added. After a further 6 days the mixture was basified to pH8 and extracted with ethyl acetate. The extracts were dried (MgSO4) and evaporated under reduced pressure. The aqueous fraction was then extracted with chloroform and the extracts dried (MgSO4) and evaporated under reduced pressure. Distillation of the combined extracts (95-115° C.; 18 mmHg) gave 8-isopropyl-8-azabicyclo[3.2.1]octan-3-one (3.37 g).

Workup

  1. additionwas added to the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extracts were dried (MgSO4)
  4. customevaporated under reduced pressure
  5. extractionThe aqueous fraction was then extracted with chloroform
  6. dry with materialthe extracts dried (MgSO4)
  7. customevaporated under reduced pressure
  8. distillationDistillation of the combined extracts (95-115° C.; 18 mmHg)

Sources & evidence

ORD record
ord-78483b4414204f07bbaa300e9e5961f4
Source dataset
uspto-grants-2001_03
Patent number
US06207676B1

Reaction notes

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