HCID 11099734, compound → HCID 57389513, compound

HRID 925131Notes

Reaction equation

HRID 925131 reaction equation
[OH:1][C@@H:2]1[CH2:7][N:6](C(OCC2C=CC=CC=2)=O)[C@H:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:4][CH2:3]1>C(O)C.[C].[Pd]>[OH:1][C@@H:2]1[CH2:7][NH:6][C@H:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 11099734HCID 11099734, compound

Product 1

HCID 57389513HCID 57389513, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 67.2 g (200.4 mmol) of (2S,5S)-1-Benzyl 2-tert-butyl 5-hydroxypiperidine-1,2-dicarboxylate in ethanol (900 mL) was added 10.1 g of 10% palladium-carbon (water content ca. 50%), followed by vigorous stirring overnight at room temperature under hydrogen atmosphere. The catalyst of the mixture was filtered through Celite-pad to concentrate the filtrate, whereby 39.3 g of the title compound was afforded as a colorless solid (yield 97%). Enantiomeric excess: 99% ee or more (CHIRALPAK AD-H, 4.6×150 mm, UV 210 nm, diethylamine/hexane/ethanol=0.1/80/20, flow rate 1 mL/min., retention time 6.3 min.).

Workup

  1. filtrationThe catalyst of the mixture was filtered through Celite-pad
  2. concentrationto concentrate the filtrate

Sources & evidence

ORD record
ord-8f4687e73b494b91a493bfe9a29fc1d9
Source dataset
uspto-grants-2016_03
Patent number
US09284273B2

Reaction notes

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