Hydrochloric Acid → Tert-butyl 4-(1-hydroxy-2-pyrrolidin-1-ylethyl)piperidinecarboxylate

HRID 2112757Notes

Reaction equation

HRID 2112757 reaction equation
[N:1]1([CH2:6][C:7]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].Cl>CO>[OH:8][CH:7]([CH:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]1)[CH2:6][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 23079654Tert-butyl 4-(2-pyrrolidin-1-ylacetyl)piperidinecarboxylate

Product 1

HCID 23079661Tert-butyl 4-(1-hydroxy-2-pyrrolidin-1-ylethyl)piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Tert-butyl 4-(2-pyrrolidin-1-ylacetyl)piperidinecarboxylate (0.33 g, 1.1 mmol) prepared according to Reference Example 12 was dissolved in methanol (5.0 mL), and was mixed with sodium borohydride (0.13 g, 3.3 mmol) added with stirring under ice-cooling, followed by stirring at room temperature for one hour. Diluted hydrochloric acid (1.0 mol/L, 0.5 mL) was added dropwise to the reaction mixture under ice-cooling, and the solvent was distilled off. The residue was diluted with water and was extracted with ethyl acetate. The organic layer was washed with brine, was dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was dried under reduced pressure and thereby yielded tert-butyl 4-(1-hydroxy-2-pyrrolidin-1-ylethyl)piperidinecarboxylate (0.24 g, 73%).

Workup

  1. additionadded
  2. temperaturecooling
  3. stirringby stirring at room temperature for one hour
  4. temperaturecooling
  5. distillationthe solvent was distilled off
  6. additionThe residue was diluted with water
  7. extractionwas extracted with ethyl acetate
  8. washThe organic layer was washed with brine
  9. dry with materialwas dried over anhydrous sodium sulfate
  10. distillationthe solvent was distilled off
  11. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-2b8eb15065314a7fbd81c85eabd4390c
Source dataset
uspto-grants-2009_04
Patent number
US07524852B2

Reaction notes

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