HCID 58564213, compound → HCID 58564201, compound

HRID 473942Notes

Reaction equation

HRID 473942 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][C:9]([C@@H:12]([N:14]3[CH2:19][CH2:18][C@:17]([CH2:26][C:27]([OH:30])([CH3:29])[CH3:28])([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[O:16][C:15]3=[O:31])[CH3:13])=[CH:8][CH:7]=2)=[CH:2]1>O=[Pt]=O.C(O)C>[OH:30][C:27]([CH3:28])([CH3:29])[CH2:26][C@@:17]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:16][C:15](=[O:31])[N:14]([C@H:12]([C:9]2[CH:10]=[CH:11][C:6]([CH:3]3[CH2:4][CH2:5][O:1][CH2:2]3)=[CH:7][CH:8]=2)[CH3:13])[CH2:19][CH2:18]1

Participants

4

Reactant 1

HCID 58564213HCID 58564213, compound

Product 1

HCID 58564201HCID 58564201, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-[(S)-1-(4-furan-3-yl-phenyl)-ethyl]-(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one (0.12 g), PtO2 (50 mg), and ethanol (15 mL) was shaken under hydrogen atmosphere (3 bar) at room temperature for 4 h. Then, the catalyst was separated by filtration and the filtrate was concentrated. The residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate 80:20->0:100) to afford the title compound.

Workup

  1. customThen, the catalyst was separated by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate 80:20->0:100)

Sources & evidence

ORD record
ord-67ec3656357f4773a6dea2b609f29347
Source dataset
uspto-grants-2014_01
Patent number
US08637505B2

Reaction notes

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