(3S,4R)-Benzyl 3-((tert-butoxycarbonyl)amino)-4-hydroxypiperidine-1-carboxylate → HCID 86340187, compound

HRID 2275022Notes

Reaction equation

HRID 2275022 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C@H:14]([OH:15])[CH2:13][CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]1[C@H:14]([OH:15])[CH2:13][CH2:12][NH:11][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86340168(3S,4R)-Benzyl 3-((tert-butoxycarbonyl)amino)-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 86340187HCID 86340187, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (3S,4R)-benzyl 3-((tert-butoxycarbonyl)amino)-4-hydroxypiperidine-1-carboxylate (1.94 g, 5.54 mmol) in ethanol (48 mL) was added to a hydrogenation flask containing 10% Pd/C (0.059 g, 0.554 mmol) that had been evacuated and back-filled with N2 (×3). The flask was again evacuated and then back-filled with H2 (×3). Enough H2 to allow complete reaction was then introduced to a burette and the system closed and the flask allowed to stir under a H2 atmosphere overnight. The reaction mixture was filtered through Celite and washed with EtOH (2×20 mL) and ethyl acetate (2×20 mL). The combined filtrate was concentrated in vacuo to afford the product as a cream oily solid—tert-butyl((3S,4R)-4-hydroxypiperidin-3-yl)carbamate (1.13 g, 5.22 mmol, 94% yield).

Workup

  1. customhad been evacuated
  2. additionback-filled with N2 (×3)
  3. customThe flask was again evacuated
  4. additionback-filled with H2 (×3)
  5. customreaction
  6. additionwas then introduced to a burette
  7. customthe system closed
  8. filtrationThe reaction mixture was filtered through Celite
  9. washwashed with EtOH (2×20 mL) and ethyl acetate (2×20 mL)
  10. concentrationThe combined filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-99351e67c59d4a91b44d596dffa626b3
Source dataset
uspto-grants-2015_09
Patent number
US09127003B2

Reaction notes

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