Sodium → HCID 68291141, compound

HRID 1408929Notes

Reaction equation

HRID 1408929 reaction equation
[Na].[OH:2][C:3]1([CH3:12])[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][C:3]([CH3:12])([OH:2])[C:4]1([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 5360545SodiumHCID 86707701HCID 86707701, compound

Product 1

HCID 68291141HCID 68291141, compoundYield 110.4%

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium (4.63 g, 201 mmol) was added in small portions over 1 h to a solution of the crude 3-hydroxy-2,2,3-trimethylcyclopentanone oxime (9.05 g, from Step 2) in n-propanol (80 mL) at 80° C. The resultant mixture stirred at 80° C. for 2 h, cooled to room temperature, poured into brine (100 mL) and extracted with dichloromethane (3×200 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated to give crude 3-amino-1,2,2-trimethylcyclopentanol (9.1 g), which was taken to the next reaction without purification.

Workup

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

Sources & evidence

ORD record
ord-ab6876bad73d45168303e27fcd3e3e68
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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