Tetrahydrofuran → HCID 86744238, compound

HRID 1087724Notes

Reaction equation

HRID 1087724 reaction equation
[CH2:1]1[O:20][C:4]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14]CC(O)=O)[C:10](=[O:19])[CH2:9]2)([O:5][CH2:6][CH3:7])[O:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:27]1CCCC1>>[CH2:1]1[O:20][C:4]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][OH:27])[C:10](=[O:19])[CH2:9]2)([O:5][CH2:6][CH3:7])[O:3][CH2:2]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 86744239HCID 86744239, compound

Product 1

HCID 86744238HCID 86744238, compoundYield 84%

Procedure

To an ice cooled solution of ethyl 4-carboxyethyl-3-oxopiperidine-1-carboxylate ethylene ketal (38 g, 0.132 mol, U.S. Pat. No. 4,278,676) in tetrahydrofurane (100 ml) is added lithium aluminium hydride pellets (2.51 g, 0.066 mol). The ice bath is removed and the reaction mixture is allowed to reach reflux temperature and is then kept at reflux temperature for 3 hours. The mixture is quenched with dilute hydrochloric acid and is diluted with dichloromethane. The mixture is washed twice with saturated brine, dried over magnesium sulphate and evaporated in vacuo to give 27.3 g (0.111 mol, 84%) of oily title product.

Workup

  1. customThe ice bath is removed
  2. temperatureto reach reflux temperature
  3. temperatureat reflux temperature for 3 hours
  4. customThe mixture is quenched with dilute hydrochloric acid
  5. additionis diluted with dichloromethane
  6. washThe mixture is washed twice with saturated brine
  7. dry with materialdried over magnesium sulphate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-d54c66f64fa944a3a15e1d2c4f39ef01
Source dataset
uspto-grants-1990_10
Patent number
US04960769

Reaction notes

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