Sodium Hydroxide → HCID 12851305, compound

HRID 1058607Notes

Reaction equation

HRID 1058607 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:13]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:14]2[CH2:19][CH2:18][CH:17]([C:20](OCC)=[O:21])[CH2:16][CH2:15]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+]>O1CCCC1>[C:7]1([C:13]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:14]2[CH2:19][CH2:18][CH:17]([CH2:20][OH:21])[CH2:16][CH2:15]2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 12851303HCID 12851303, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12851305HCID 12851305, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of 10.6 g of lithium aluminium hydride in 300 ml of dried tetrahydrofuran, a solution of 112 g of ethyl N-triphenylmethyl-4-piperidine-carboxylate in 400 ml of dried tetrahydrofuran was added dropwise under ice-cooling, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was added dropwise with a mixture of tetrahydrofuran and 10% aqueous sodium hydroxide solution under ice-cooling. An insoluble matter was filtered off and washed with tetrahydrofuran. The filtrates were combined and concentrated to give a colorless solid. The colorless solid was washed with methanol to give 84.2 g of colorless crystals. Recrystallization from methanol gave colorless crystals having the melting point of from 92 to 99.5° C.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. filtrationAn insoluble matter was filtered off
  4. washwashed with tetrahydrofuran
  5. concentrationconcentrated
  6. customto give a colorless solid
  7. washThe colorless solid was washed with methanol

Sources & evidence

ORD record
ord-67035d049b454cf9b14543eca6ad8764
Source dataset
uspto-grants-2003_02
Patent number
US06518265B1

Reaction notes

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