Benzyl 4-((1R,2S)-2-(2-hydroxyethyl)cyclopropyl)piperidine-1-carboxylate → 2-((1S,2R)-2-(piperidin-4-yl)cyclopropyl)ethanol

HRID 1850794Notes

Reaction equation

HRID 1850794 reaction equation
[OH:1][CH2:2][CH2:3][C@@H:4]1[CH2:6][C@@H:5]1[CH:7]1[CH2:12][CH2:11][N:10](C(OCC2C=CC=CC=2)=O)[CH2:9][CH2:8]1.[H][H]>CCOC(C)=O.CO.[Pd]>[NH:10]1[CH2:11][CH2:12][CH:7]([C@H:5]2[CH2:6][C@H:4]2[CH2:3][CH2:2][OH:1])[CH2:8][CH2:9]1

Participants

5

Reactant 2

HCID 70856295Benzyl 4-((1R,2S)-2-(2-hydroxyethyl)cyclopropyl)piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 867111782-((1S,2R)-2-(piperidin-4-yl)cyclopropyl)ethanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

Benzyl 4-((1R,2S)-2-(2-hydroxyethyl)cyclopropyl)piperidine-1-carboxylate (10 g, 33 mmol) was dissolved in 100 mL of EtOAc/MeOH (1:1 v/v), to which was added 1 g of 5% Pd/C and apply hydrogen balloon. After stirring at rt for 1 h, the reaction mixture was filtered through Celite to give the product that was used in the next step without further purification. Rf was 0 @ 50% EtOAc in hexanes (blue spot on CAM stain).

Workup

  1. filtrationthe reaction mixture was filtered through Celite
  2. customto give the product that
  3. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-ee32e3bf9ea842ccb2f962c8c8d30a11
Source dataset
uspto-grants-2015_02
Patent number
US08957062B2

Reaction notes

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