Aluminium lithium hydride → HCID 66746365, compound

HRID 2279415Notes

Reaction equation

HRID 2279415 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12](=[O:26])[NH:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]([CH:23]2[CH2:25][CH2:24]2)=[O:22])[CH2:16][CH2:15]1)([CH3:10])([CH3:9])[CH3:8]>O1CCCC1>[C:7]([O:11][C:12](=[O:26])[NH:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH:21]([CH:23]2[CH2:24][CH2:25]2)[OH:22])[CH2:16][CH2:15]1)([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66746563HCID 66746563, compound

Product 1

HCID 66746365HCID 66746365, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium aluminium hydride (1.0M solution in tetrahydrofuran, 1.41 mL, 1.41 mmol, 1.0 eq) is added at 0° C. to a stirred solution of [1-(2-cyclopropyl-2-oxo-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (420 mg, 1.41 mmol, 1.0 eq) in tetrahydrofuran (25 mL). After 2 hours stirring at 0° C., the reaction mixture is cautiously quenched with ice-water (5 mL). Tetrahydrofuran in evaporated and the crude is extracted with dichloromethane (3×30 mL) and water (30 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford [1-(2-cyclopropyl-2-hydroxy-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester as a white solid (373 mg, 84% yield).

Workup

  1. customthe reaction mixture is cautiously quenched with ice-water (5 mL)
  2. customTetrahydrofuran in evaporated
  3. extractionthe crude is extracted with dichloromethane (3×30 mL) and water (30 mL)
  4. dry with materialThe combined organic layers are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-825f39d89dcb4eb48dc2d85c37d452af
Source dataset
uspto-grants-2015_09
Patent number
US09133219B2

Reaction notes

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