Aluminium lithium hydride → HCID 66889504, compound

HRID 253233Notes

Reaction equation

HRID 253233 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](OC)=[O:10])=[CH:5][C:4]=1[O:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([O:13][CH2:14][CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[CH2:17][CH2:16]2)[CH:5]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66890897HCID 66890897, compound

Product 1

HCID 66889504HCID 66889504, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1,1-Dimethylethyl 4-[({2-(methyloxy)-5-[(methyloxy)carbonyl]phenyl}oxy) methyl]piperidine-1-carboxylate (3.34 g, 8.8 mmol) was dissolved in THF (30 mL) and the resulting solution was cooled with an ice bath. A solution of LAH in THF (1 M, 8.8 mmol, 8.8 mL) was added by syringe. The reaction vessel was removed from the ice bath, and the reaction mixture was allowed to warm to rt. After 2 h at rt, the mixture was quenched by cautious sequential addition of water (0.33 mL), 15% NaOH (aq) (0.33 mL), and water (1 mL). During the quench, a white precipitate formed. The solid was removed by filtration through celite and was rinsed with ether. The combined organic layers were washed with dilute hydrochloric acid to then dried over sodium sulfate, filtered, and concentrated to provide 1.88 g of 1,1-dimethylethyl 4-({[5-(hydroxymethyl)-2-(methyloxy)phenyl]oxy}methyl)piperidine-1-carboxylate (5.4 mmol, 61% yield). 1H NMR (400 MHz, CDCl3): δ6.93-6.85 (m, 3H), 4.62 (d, 2H), 4.15 (br m, 2H), 3.87 (m, 2H), 3.86 (s, 3H), 2.76 (br m, 2H), 2.06 (m, 1H), 1.88 (br d, 2H), 1.47 (s, 9H), 1.28 (m, 2H).

Workup

  1. temperaturethe resulting solution was cooled with an ice bath
  2. customThe reaction vessel was removed from the ice bath
  3. customthe mixture was quenched by cautious sequential addition of water (0.33 mL), 15% NaOH (aq) (0.33 mL), and water (1 mL)
  4. customDuring the quench, a white precipitate formed
  5. customThe solid was removed by filtration through celite
  6. washwas rinsed with ether
  7. washThe combined organic layers were washed with dilute hydrochloric acid
  8. dry with materialto then dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-0ee8f054221e447b8d3baf200a1b2033
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

Loading…