Sodium borohydride → 3-(2-Hydroxy-ethyl)-3-hydroxymethyl-piperidin-2-one

HRID 656474Notes

Reaction equation

HRID 656474 reaction equation
C([O:3][C:4]([C:6]1([CH2:13][C:14](OCC)=[O:15])[CH2:11][CH2:10][CH2:9][NH:8][C:7]1=[O:12])=O)C.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+]>CO>[OH:15][CH2:14][CH2:13][C:6]1([CH2:4][OH:3])[CH2:11][CH2:10][CH2:9][NH:8][C:7]1=[O:12]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 685748043-Ethoxycarbonylmethyl-2-oxo-piperidine-3-carboxylic acid ethyl ester

Product 1

HCID 685766973-(2-Hydroxy-ethyl)-3-hydroxymethyl-piperidin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1 mmol of 3-ethoxycarbonylmethyl-2-oxo-piperidine-3-carboxylic acid ethyl ester, 1 mmol of calcium chloride, and 5 ml of methanol is cooled to 0° C. and treated with one portion of 1 mmol of sodium borohydride, keeping the temperature at 0-5° C. with cooling for 2 hours. The mixture is allowed to warm to room temperature overnight. The solids are filtered and washed with methanol. The methanol filtrate is concentrated. The residue is triturated with diethyl ether and decanted. The residue is treated with water and the separated solid is filtered and washed with water. The aqueous filtrates are saturated with potassium carbonate and extracted with dichloromethane (3×) methylene chloride. The combined organic extracts and are dried over potassium carbonate, filtered, and concentrated. From the residue the crude title compound is identified on the basis of the Rf value. The title compound is used without further purification in the next stage.

Workup

  1. customat 0-5° C.
  2. temperaturewith cooling for 2 hours
  3. filtrationThe solids are filtered
  4. washwashed with methanol
  5. concentrationThe methanol filtrate is concentrated
  6. customThe residue is triturated with diethyl ether
  7. customdecanted
  8. additionThe residue is treated with water
  9. filtrationthe separated solid is filtered
  10. washwashed with water
  11. extractionextracted with dichloromethane (3×) methylene chloride
  12. dry with materialThe combined organic extracts and are dried over potassium carbonate
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customThe title compound is used without further purification in the next stage

Sources & evidence

ORD record
ord-85fab8cae95f4513a83f85154e510c64
Source dataset
uspto-grants-2011_12
Patent number
US08071773B2

Reaction notes

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