Water → HCID 59303556, compound

HRID 1928886Notes

Reaction equation

HRID 1928886 reaction equation
C(O[C:6](=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]1)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:6][NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 45076484[1-(2-Hydroxy-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

Product 1

HCID 59303556HCID 59303556, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of [1-(2-hydroxy-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (CAS m 558443-53-1) (5.71 g, 23 mmol) in tetrahydrofuran (100 ml) at 23° C. was added in portions lithium aluminum hydride (2.66 g, 70 mmol) and the mixture was stirred at 70° C. for 18 h. Then the reaction was cooled to 0° C., water (2.66 ml) was added very slowly, then NaOH 15% (7.98 ml) and water (2.66 ml). The mixture was stirred at 23° C. for 1.5 h, the precipitate was filtered off, washed with tetrahydrofuran and the organic layer was evaporated totally to give the title compound as a white solid (3.7 g, 100%), MS (ISP) m/e=159.3 [(M+H)+].

Workup

  1. temperatureThen the reaction was cooled to 0° C.
  2. stirringThe mixture was stirred at 23° C. for 1.5 h
  3. filtrationthe precipitate was filtered off
  4. washwashed with tetrahydrofuran
  5. customthe organic layer was evaporated totally

Sources & evidence

ORD record
ord-f706bef6a8d14cf3ab32a18d2dfaa3f2
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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