Potassium Hydroxide → rac-(3R,4R)-4-(benzylamino)piperidin-3-ol

HRID 345540Notes

Reaction equation

HRID 345540 reaction equation
[OH-].[K+].[OH:3][C@H:4]1[C@H:9]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7][N:6](C(OCC)=O)[CH2:5]1>CC(O)C>[C:12]1([CH2:11][NH:10][C@@H:9]2[CH2:8][CH2:7][NH:6][CH2:5][C@H:4]2[OH:3])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 13677850Ethyl trans-3-hydroxy-4-[(phenylmethyl)amino]-1-piperidinecarboxylate

Product 1

HCID 13677852rac-(3R,4R)-4-(benzylamino)piperidin-3-olYield 70.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 195.4 parts of potassium hydroxide and 1065 parts of 2-propanol was stirred and warmed till all solid entered solution. After cooling to room temperature, 97 parts of ethyl trans-3-hydroxy-4-[(phenylmethyl)amino]-1-piperidinecarboxylate were added and the whole was stirred and refluxed for 4 hours. The reaction mixture was evaporated to dry and 500 parts of water were added. The whole was concentrated to a volume of about 300 parts. After cooling to room temperature, the product was extracted with dichloromethane. The extract was washed with water, dried, filtered and evaporated. The oily residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 51 parts (70.8%) of trans-4-[(phenylmethyl)amino]-3-piperidinol; mp. 136° C. (intermediate 39).

Workup

  1. temperaturewarmed till all solid
  2. stirringthe whole was stirred
  3. temperaturerefluxed for 4 hours
  4. customThe reaction mixture was evaporated
  5. customto dry
  6. addition500 parts of water were added
  7. concentrationThe whole was concentrated to a volume of about 300 parts
  8. temperatureAfter cooling to room temperature
  9. extractionthe product was extracted with dichloromethane
  10. washThe extract was washed with water
  11. customdried
  12. filtrationfiltered
  13. customevaporated
  14. customThe oily residue was crystallized from acetonitrile
  15. filtrationThe product was filtered off
  16. customdried

Sources & evidence

ORD record
ord-59ae029039504f91b9acf1fc982c25d9
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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