Sodium Hydroxide → HCID 18442924, compound

HRID 1434600Notes

Reaction equation

HRID 1434600 reaction equation
[C:1]1([CH:7]([CH:14]2[CH2:19][CH2:18][N:17]([O:20][C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22])[CH2:16][CH2:15]2)[CH2:8][C:9](OCC)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1>[C:1]1([CH:7]([CH:14]2[CH2:19][CH2:18][N:17]([O:20][C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22])[CH2:16][CH2:15]2)[CH2:8][CH:9]=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 18442932HCID 18442932, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18442924HCID 18442924, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 3-phenyl-3-(1-tert-butylcarbonyloxypiperidin-4-yl)propionoate (5.3 g, 14.6 mmol) in THF (100 mL) was added lithium aluminium hydride (14.6 mL, 1M, 14.6 mmol) dropwise over 20 min. The resulting mixture was stirred at 0° C. for 1 h. 2M aqueous sodium hydroxide (20 mL) was added dropwise. The mixture was filtered through Celite®, washing with ethyl acetate (3×25 mL). The filtrate and washings were combined and evaporated. The residue was dissolved in ethyl acetate (100 mL) and the resulting solution washed with water (3×50 mL), dried and evaporated to give the sub-titled compound (4.6 g); NMR: 0.9-1 (m, 2H) 1.25 (m, 1H) 1.35 (s, 9H) 1.5-2 (m, 5H) 2.6 (m, 2H) 3.1 (m, 2H) 3.8-4 (m, 2H) 4.2 (t, 1H).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. washwashing with ethyl acetate (3×25 mL)
  3. customevaporated
  4. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  5. washthe resulting solution washed with water (3×50 mL)
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-93f7c48528e540ff8d7d796eb92728eb
Source dataset
uspto-grants-2009_11
Patent number
US07615555B2

Reaction notes

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