Ethyl Acetate → 3-Chloro-6,7-dihydro-5H-cyclopenta[B]pyridin-7-OL

HRID 1626130Notes

Reaction equation

HRID 1626130 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([O:11]C(=O)C)[CH2:7][CH2:8][C:9]=2[CH:10]=1.[OH-].[Na+].CCCCCCC.C(OCC)(=O)C>CO.O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([OH:11])[CH2:7][CH2:8][C:9]=2[CH:10]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 8900HeptaneHCID 14798Sodium HydroxideHCID 580827683-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl Acetate

Product 1

HCID 580828163-Chloro-6,7-dihydro-5H-cyclopenta[B]pyridin-7-OLYield 91.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of acetic acid 3-chloro-6,7-dihydro-5H-[1]pyrindin-7-yl ester (1.57 g, 7.42 mmol) in methanol (35.7 ml) was treated with a solution of sodium hydroxide (1M; 8.9 ml). The mixture was stirred at room temperature for 1.5 hours. The reaction was followed by TLC (silica gel, heptane:ethyl acetate=1:1; UV detection 254 nm). After completion, the reaction mixture was treated with water and extracted with dichloromethane. The combined organic layers were dried over sodium sulphate, then evaporated leaving a dark red liquid (1.15 g, 91% yield) which crystallised on standing. Following NMR the product was pure enough for the next step of the synthesis. MS (ISP): m/z=170 [M+H]+.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic layers were dried over sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-872d035d355f4ebd8f016c72fefc0a7f
Source dataset
uspto-grants-2014_07
Patent number
US08785436B2

Reaction notes

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