Aluminium lithium hydride → HCID 59438412, compound

HRID 2177474Notes

Reaction equation

HRID 2177474 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O[C:15]([N:17]1[CH2:22][CH2:21][CH2:20][C:19]([N:29]=[N+]=[N-])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:18]1)=O)C1C=CC=CC=1>C1COCC1>[CH3:15][N:17]1[CH2:22][CH2:21][CH2:20][C:19]([NH2:29])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:18]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59438450HCID 59438450, compound

Product 1

HCID 59438412HCID 59438412, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

To a suspension of 126 mg (3.15 mmol) LiAlH4 in THF (2.7 ml) at temperature below 10° C. was added dropwise a solution of 530 mg (1.576 mmol) rac-3-azido-3-phenyl-piperidine-1-carboxylic acid benzyl ester in THF (5.3 ml). The ice bath was removed. The temperature rose to 35° C. The mixture was then heated in a 65° C. oil bath for 1 hour. The mixture was cooled to 0° C. Water (125 ul), NaOH 5N (125 ul) and finally water (0.375 ml) were added dropwise maintaining the temperature below 10° C. The mixture was diluted with ethyl acetate. Sodium sulfate was added. The mixture was filtered and the filtrate was concentrated in vacuo. The crude oil was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%) to provide 0.14 g (47%) of the title compound as a yellow oil. MS (m/e): 191.5 (M+H+)

Workup

  1. customThe ice bath was removed
  2. customrose to 35° C
  3. temperatureThe mixture was cooled to 0° C
  4. additionWater (125 ul), NaOH 5N (125 ul) and finally water (0.375 ml) were added dropwise
  5. temperaturemaintaining the temperature below 10° C
  6. additionThe mixture was diluted with ethyl acetate
  7. additionSodium sulfate was added
  8. filtrationThe mixture was filtered
  9. concentrationthe filtrate was concentrated in vacuo
  10. customThe crude oil was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%)

Sources & evidence

ORD record
ord-8a26abdc75a344b787b5d888df4b359a
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

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