HCID 11099734, compound → HCID 57389513, compound

HRID 710957Notes

Reaction equation

HRID 710957 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 97.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of (2S,5S)-1-benzyl 2-tert-butyl 5-hydroxypiperidine-1,2-dicarboxylate (67.2 g) described in Reference Example 1 in ethanol (900 mL) was added 10% palladium-carbon (water content approximately 50%, 10.1 g), followed by vigorously stirring under an hydrogen atmosphere at room temperature overnight. The catalyst of the mixture was filtered through Celite, followed by concentrating the filtrate, thereby 39.3 g of the title compound was afforded as the 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
  2. concentrationby concentrating the filtrate

Sources & evidence

ORD record
ord-840ec5ded4ed4b22a86513a49437eb21
Source dataset
uspto-grants-2015_11
Patent number
US09181250B2

Reaction notes

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