Water → O-(2,2,5,5-tetramethyl-1-cyclopentyl)-1-amino-1-hydroxymethylcyclopropane

HRID 255468Notes

Reaction equation

HRID 255468 reaction equation
C([NH:8][C:9]1([CH2:12][O:13][CH:14]2[C:18]([CH3:20])([CH3:19])[CH2:17][CH2:16][C:15]2([CH3:22])[CH3:21])[CH2:11][CH2:10]1)(OC(C)(C)C)=O.O.[OH-].[K+]>FC(F)(F)C(O)=O>[CH3:21][C:15]1([CH3:22])[CH2:16][CH2:17][C:18]([CH3:19])([CH3:20])[CH:14]1[O:13][CH2:12][C:9]1([NH2:8])[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 20165730N-Boc-O-(2,2,5,5-tetramethyl-1-cyclopentyl)-1-amino-1-hydroxymethylcyclopropane

Product 1

HCID 20165720O-(2,2,5,5-tetramethyl-1-cyclopentyl)-1-amino-1-hydroxymethylcyclopropane

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

N-Boc-O-(2,2,5,5-tetramethyl-1-cyclopentyl)-1-amino-1-hydroxymethylcyclopropane is dissolved in trifluoroacetic acid and stirred overnight. The solution is poured into water and neutralized with 20% aqueous KOH. The mixture is extracted with ethyl acetate, dried over MgSO4, filtered and evaporated to give O-(2,2,5,5-tetramethyl-1-cyclopentyl)-1-amino-1-hydroxymethylcyclopropane.

Workup

  1. extractionThe mixture is extracted with ethyl acetate
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-8a8482ad69ca435c88ac9a50c23b1425
Source dataset
uspto-grants-1987_10
Patent number
US04698231

Reaction notes

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