Water → HCID 85860577, compound

HRID 1767052Notes

Reaction equation

HRID 1767052 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[CH2:7][CH:6]([C:11](O)=[O:12])[CH2:5][C:4]=2[N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[CH2:7][CH:6]([CH2:11][OH:12])[CH2:5][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2×HCID 21260374HCID 21260374, compound

Product 1

HCID 85860577HCID 85860577, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.83 g (9.26 mmol) of (+/−)2-chloro-6,7-dihydro-5H-[1]pyrindine-6-carboxylic acid (prepared by analogy to the method described in WO 99/02517) in 50 ml of anhydrous tetrahydrofuran under argon was added 0.52 g (13.89 mmol) of lithium aluminium hydride. The resulting mixture was stirred at room temperature for 2 h. Excess of lithium aluminium hydride was hydrolysed with 2.13 ml of water and 0.53 ml of sodium hydroxide (15%). The precipitate was filtered off and washed with diethyl ether, the filtrate was evaporated to give 1.61 g (95%) of product as an oil.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with diethyl ether
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-617c32e135bc4f1297f1ed93b445ece6
Source dataset
uspto-grants-2007_06
Patent number
US07232827B2

Reaction notes

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