Tetrahydrofuran → HCID 22020939, compound

HRID 876046Notes

Reaction equation

HRID 876046 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.[NH2:12][C:13]1([C:26](O)=[O:27])[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14]1.[OH-].[Na+]>O>[NH2:12][C:13]1([CH2:26][OH:27])[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 14803624-Amino-1-benzylpiperidine-4-carboxylic AcidHCID 21226445Aluminium lithium hydride

Product 1

HCID 22020939HCID 22020939, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Lithium aluminum hydride (1.94 g, 51.2 mmol) was added to a THF (100 mL) solution of 4-amino-1-benzylpiperidine-4-carboxylic acid [Albert, J. S. et al. J. Med. Chem. 2002, 45, (18), 3972-3983] (390) (3.00 g, 12.8 mmol). The resulting mixture was stirred for 1.5 h at reflux. The reaction was cooled to room temperature and the following additions were made slowly: 2 mL of water followed by 2 mL of 1 N NaOH, and finally 4 mL of water. The mixture was then filtered and concentrated to give compound 391 as a thick clear oil (2.22 g, 79% yield). The material was used in the next step without further purification. LCMS-ESI (POS), M/Z, M+1: Found 221, Calculated 221.

Workup

  1. temperatureat reflux
  2. filtrationThe mixture was then filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-654e714951304f0c807778420374e8c1
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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