Sodium → HCID 68291552, compound

HRID 1408927Notes

Reaction equation

HRID 1408927 reaction equation
[Na].[OH:2][CH:3]1[CH2:7][CH2:6][C:5](=[N:8]O)[C:4]1([CH3:11])[CH3:10]>C(O)CC.[Cl-].[Na+].O>[NH2:8][CH:5]1[CH2:6][CH2:7][CH:3]([OH:2])[C:4]1([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 5360545SodiumHCID 86707700HCID 86707700, compound

Product 1

HCID 68291552HCID 68291552, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium (2.312 g, 101 mmol) was added in small portions over 30 min to a solution of 3-hydroxy-2,2-dimethylcyclopentanone oxime (3.60 g, 25.1 mmol, from Step 2) in n-propanol (50 mL) at 80° C. The resultant mixture was heated to 100° C. for 2 h, cooled to room temperature, poured into brine (100 mL) and extracted with ethyl acetate (3×200 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated to give crude 3-amino-2,2-dimethylcyclopentanol (3.10 g), which was used in the next reaction without purification.

Workup

  1. extractionextracted with ethyl acetate (3×200 mL)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-aa5bcee0415140bd8a718c14d45d2970
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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