Aluminium lithium hydride → HCID 58442823, compound

HRID 41647Notes

Reaction equation

HRID 41647 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:18]([C:19](OC)=[O:20])=[CH:17][S:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:18]([CH2:19][OH:20])=[CH:17][S:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58442821HCID 58442821, compound

Product 1

HCID 58442823HCID 58442823, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of 4-(4-methoxycarbonylthiophen-3-yl)-piperidine-1-carboxylic acid t-butyl ester (100 mg, 310 μmol, 1.0 eq.) in THF (5 mL) was combined with a solution of LiAlH4 (23 mg) under nitrogen. The resulting solution was stirred for 30 minutes while the temperature was maintained at 0-5° C. in an ice/salt bath. The reaction was then quenched by the addition of water (50 μL) and aqueous NaOH (150 μL). The solids were filtered and the filtrate was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with EtOAc/PE (1:10) to yield the titled compound (50 mg) as a colorless oil. MS m/z: [M+H]+ calcd for C15H24NO3S, 298. found 298.

Workup

  1. customThe reaction was then quenched by the addition of water (50 μL) and aqueous NaOH (150 μL)
  2. filtrationThe solids were filtered
  3. concentrationthe filtrate was concentrated under vacuum
  4. washeluted with EtOAc/PE (1:10)

Sources & evidence

ORD record
ord-691f27d0f439434d9e6decbc20585618
Source dataset
uspto-grants-2013_09
Patent number
US08530663B2

Reaction notes

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