Sodium Hydroxide → 1-(Cyclohexylamino)-1-(hydroxymethyl)cyclopentane

HRID 276258

Reaction equation

HRID 276258 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Al+3].[Cl-].[Cl-].[Cl-].[CH2:11]1[C:15]2([NH:24][C:18]3([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[O:17][CH2:16]2)[CH2:14][CH2:13][CH2:12]1.[OH-].[Na+]>C1COCC1.O>[CH:18]1([NH:24][C:15]2([CH2:16][OH:17])[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 1831620513-Oxa-6-azadispiro[4.1.5.2]tetradecaneHCID 21226445Aluminium lithium hydride

Product 1

HCID 183161421-(Cyclohexylamino)-1-(hydroxymethyl)cyclopentaneYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of LiAlH4 (0.93 g, 24.4 mmol) and AlCl3 (3.24 g, 24.4 mmol) in THF at 4° C. was added dropwise a solution of 14-aza-7-oxadispiro[4.2.5.1]tetradecane (2.38 g, 12,2 mmol) in THF (15 mL). The resulting mixture was warmed to 20° C. and stirred for 45 min., then cooled to 4° C. Water (5 mL) was slowly added to quench the reaction and a 1N NaOH solution (85 mL) was added to dissolve the resulting solids. The resulting solution was extracted with Et2O (200 mL). The organic layer was dried (Na2SO4) and concentrated under reduced pressure to yield 1-(cyclohexylamino)-1-(hydroxymethyl)cyclopentane 1.89 g (79%): GC-MS m/z 197 (M+).

Workup

  1. temperaturecooled to 4° C
  2. customto quench
  3. customthe reaction
  4. dissolutionto dissolve the resulting solids
  5. extractionThe resulting solution was extracted with Et2O (200 mL)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6e68bfb8a2134a28b6bf190ddde2c6b9
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Linked notes

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