Water → tert-Butyl 3-(3-hydroxypropyl)piperidine-1-carboxylate

HRID 2095430Notes

Reaction equation

HRID 2095430 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][CH2:15][C:16](O)=[O:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[H][H]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][CH2:15][CH2:16][OH:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 27568241-Boc-piperidin-3-yl-propionic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 21188640tert-Butyl 3-(3-hydroxypropyl)piperidine-1-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of commercially available 3-[1-(tert-butoxycarbonyl)-3-piperidinyl]propionic acid (2.57 g, 10.0 mmol) in 100 mL of anhydrous THF was added slowly a solution of BH3.THF complex in THF (1.0 M, 20 mL, 2.0 equiv) at room temperature under N2. The solution was stirred for 16 h at room temperature. Water was added carefully (hydrogen evolution!), and the resulting solution was concentrated under reduced pressure. The residue was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure to give the alcohol (2.35 g, 97%) as a colorless oil. LC-MS (ESI) m/z 244 (M+H+).

Workup

  1. concentrationthe resulting solution was concentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-52ae5837b35d4543a226a668dc0e7eca
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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