Aluminium lithium hydride → HCID 58724153, compound

HRID 2356211Notes

Reaction equation

HRID 2356211 reaction equation
[C:1]1([S:11]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=3[C:22](OC)=[O:23])[CH2:16][CH2:15]2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]1([S:11]([N:14]2[CH2:15][CH2:16][CH:17]([C:20]3[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=3[CH2:22][OH:23])[CH2:18][CH2:19]2)(=[O:12])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58724174HCID 58724174, compound

Product 1

HCID 58724153HCID 58724153, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(1-(naphthalen-1-ylsulfonyl)piperidin-4-yl)benzoate (80 mg, 0.02 mmol) was dissolved in 1 mL of anhydrous THF under nitrogen protection. 0.4 mL of LiAlH4 (1.0M solution in THF) was added to the solution through a syringe at −78° C. After 30 minutes, the reaction mixture was quenched with MeOH, evaporated to dryness, and extracted with EtOAc and 0.1 N tartaric acid solution in water. The organic layer was then dried over Na2SO4, and the solvent was removed. The title compound was obtained in 60% yield after purification using preparative HPLC. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.58 (dd, J=12.38, 3.54 Hz, 2 H) 1.67-1.74 (m, 2 H) 2.52-2.61 (m, 2 H) 2.73-2.81 (m, 2 H) 3.88 (d, J=12.13 Hz, 2 H) 4.42 (d, J=3.79 Hz, 2 H) 4.96 (s, 1 H) 7.08-7.19 (m, 3 H) 7.24-7.29 (m, 1 H) 7.66-7.78 (m, 4 H) 8.13 (d, J=8.84 Hz, 1H) 8.17 (d, J=7.33 Hz, 1 H) 8.31 (d, J=8.08 Hz, 1 H) 8.75 (d, J=8.59 Hz, 1 H); ESI-MS: m/z 382.1 (M+H)+.

Workup

  1. customthe reaction mixture was quenched with MeOH
  2. customevaporated to dryness
  3. extractionextracted with EtOAc and 0.1 N tartaric acid solution in water
  4. dry with materialThe organic layer was then dried over Na2SO4
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-d2f19f8f268a40f4bdb59ea9f5a24022
Source dataset
uspto-grants-2010_07
Patent number
US07759339B2

Reaction notes

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