Methanol → 3-(6-Chloropyridin-3-yl)cyclopentanol

HRID 646636Notes

Reaction equation

HRID 646636 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][C:10](=[O:13])[CH2:9]2)=[CH:4][CH:3]=1.CO.[BH4-].[Na+]>C(Cl)Cl.O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 592659583-(6-Chloropyridin-3-yl)cyclopentanone

Product 1

HCID 592659373-(6-Chloropyridin-3-yl)cyclopentanolYield 101.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-(6-Chloropyridin-3-yl)cyclopentanone (0.27 g, 1.4 mmol) was dissolved in CH2Cl2 (10 mL) and MeOH (1 mL) in a 100 mL round bottomed flask and treated with NaBH4 (0.05 g, 1.4 mmol) with stirring at room temperature. After 15 min. the reaction was diluted with water, the layers separated, the aqueous phase extracted with CH2Cl2, and the combined organic layers dried (Na2SO4), filtered and concentrated to give 3-(6-chloropyridin-3-yl)cyclopentanol (0.28 g, 100%) as an oily mixture of cis and trans isomers: LC/MS (ESI) m/z 197, 1H NMR (300 MHz, CDCl3) δ 8.27 (m, 2H), 7.65-7.48 (m, 2H), 7.26 (m, 2H), 4.52 (m, 2H), 3.49-2.99 (m, 2H), 2.51-2.01 (m, 4H), 1.99-1.40 m, 10H).

Workup

  1. customthe layers separated
  2. extractionthe aqueous phase extracted with CH2Cl2
  3. dry with materialthe combined organic layers dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-22a3f49d1a844ff88717881d6f95cf05
Source dataset
uspto-grants-2010_04
Patent number
US07705156B2

Reaction notes

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