Water → HCID 920114, compound

HRID 1864009Notes

Reaction equation

HRID 1864009 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][CH2:8][C@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15](OC(C)(C)C)=O)[CH2:10]1.O.[OH-].[Na+]>CCOCC.C1COCC1>[CH3:15][N:11]1[CH2:12][CH2:13][CH2:14][C@H:9]([CH2:8][OH:7])[CH2:10]1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 1514448tert-Butyl (3S)-3-(hydroxymethyl)piperidine-1-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 920114HCID 920114, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of lithium aluminum hydride (10.5 ml of 1M solution in THF, 10.5 mmol) in ether (15 mL) at 20° C. was added dropwise a solution of 1,1-dimethylethyl (3S)-3-(hydroxymethyl)-1-piperidinecarboxylate (1.50 g, 7.0 mmol) in THF (5 mL). After 1.5 h at room temperature, water (0.4 mL) was added followed by 15% aqueous sodium hydroxide solution (0.4 mL) then water (1.2 mL). This was stirred 20 min then filtered. The filtrate was concentrated under reduced pressure to give 0.87 g used in the next step without further purification. MS (ES+) m/z 130.2 (M+H)+.

Workup

  1. filtrationthen filtered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customto give 0.87 g
  4. customused in the next step without further purification

Sources & evidence

ORD record
ord-ded0f74149c44746aa96d3d4f7096f95
Source dataset
uspto-grants-2009_12
Patent number
US07625890B2

Reaction notes

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