Water → HCID 59053607, compound

HRID 383923Notes

Reaction equation

HRID 383923 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH:10]3[C:17](OCC)=[O:18])[CH2:8]1)[CH2:14]2.O.[OH-].[Na+]>C1COCC1>[N:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH:10]3[CH2:17][OH:18])[CH2:8]1)[CH2:14]2

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68593715HCID 68593715, compound

Product 1

HCID 59053607HCID 59053607, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LAH in THF was added dropwise a solution of ethyl 1-azatricyclo[3.3.1.13,7]decane-4-carboxylate in THF at 0 to 5° C., followed by stirring at the same temperature for 1 hour. Under ice-cooling, to the reaction mixture were added water, a 15% aqueous NaOH solution, and then water in this order. The insolubles were removed by filtration through Celite, followed by washing with EtOAc. The filtrate was dried over MgSO4 and then concentrated under reduced pressure to obtain 1-azatricyclo[3.3.1.13,7]decan-4-yl methanol as a colorless oily substance.

Workup

  1. temperatureUnder ice-cooling, to the reaction mixture
  2. customThe insolubles were removed by filtration through Celite
  3. washby washing with EtOAc
  4. dry with materialThe filtrate was dried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-13754502ae0c4071aadfb345397cdb4c
Source dataset
uspto-grants-2013_02
Patent number
US08367696B2

Reaction notes

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