HCID 18665753, compound → HCID 18665735, compound

HRID 365458Notes

Reaction equation

HRID 365458 reaction equation
[C:1]1([CH:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([C:15](OCC)=[O:16])[CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[C:1]1([CH:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([CH2:15][OH:16])[CH2:10]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 18665753HCID 18665753, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18665735HCID 18665735, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Ethyl 1-(2,2-Diphenylethyl)-3(S)-piperidine carboxylate (4.90 g, 0.014 mol) dissolved in dry ether (40 mL) was added to a suspension of lithium aluminum hydride (1.93 g, 0.051 mol) in dry ether (40 mL). The solution was refluxed until the starting material was consumed and then was quenched with saturated potassium sodium tartrate solution (100 mL) and stirred for 2 hr. The layers were separated and the aqueous layer extracted with ether (2×). The combined organic extracts were dried (MgSO4) and concentrated to yield the title compound without further purification.

Workup

  1. temperatureThe solution was refluxed until the starting material
  2. customwas consumed
  3. customwas quenched with saturated potassium sodium tartrate solution (100 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer extracted with ether (2×)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b0850133071c426db5b44a3e0f37902f
Source dataset
uspto-grants-2000_10
Patent number
US06127366

Reaction notes

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