Aluminium lithium hydride → HCID 67983173, compound

HRID 530880Notes

Reaction equation

HRID 530880 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][C:5]1([C:18](OC)=[O:19])[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[CH:22][C:3]=1[CH2:4][C:5]1([CH2:18][OH:19])[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[O:12])[CH2:6]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 679853881-tert-Butyl 3-methyl 3-(2-fluorobenzyl)piperidine-1,3-dicarboxylate

Product 1

HCID 67983173HCID 67983173, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a flask, 1-tert-butyl 3-methyl 3-(2-fluorobenzyl)piperidine-1,3-dicarboxylate (1.41 g, 4.0 mmol) was dissolved in tetrahydrofuran (20 mL). Lithium aluminum hydride (8.03 mmol) was added to the flask. The reaction was stirred for an hour at room temperature. Upon completion, the reaction was quenched with ethyl acetate (10 ml) drop-wise. Water (30 mL) was added to the reaction. The reaction mixture then was extracted 3 times with ethyl acetate (50 mL). The organic layers were combined, were dried with sodium sulfate, concentrated and purified using flash chromatography (0 60% ethyl acetate in hexane) to give the titled compound (1.29 g).

Workup

  1. customUpon completion, the reaction was quenched with ethyl acetate (10 ml) drop-wise
  2. additionWater (30 mL) was added to the reaction
  3. extractionThe reaction mixture then was extracted 3 times with ethyl acetate (50 mL)
  4. dry with materialwere dried with sodium sulfate
  5. concentrationconcentrated
  6. custompurified

Sources & evidence

ORD record
ord-576b86b8857e4aab8e42bee19e5bccea
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

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