HCID 58497898, compound → HCID 44538094, compound

HRID 1519216Notes

Reaction equation

HRID 1519216 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C@H:2]1[C:11]([N:13]1[CH2:20][CH2:19][C@:18]2([CH3:23])[C@@H:21]([CH3:22])[C@H:14]1[CH2:15][C:16]1[CH:27]=[CH:26][C:25](OS(C(F)(F)F)(=O)=O)=[CH:24][C:17]=12)=[O:12]>CO.C(OCC)(=O)C.[Pd]>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C@H:2]1[C:11]([N:13]1[CH2:20][CH2:19][C@:18]2([CH3:23])[C@@H:21]([CH3:22])[C@H:14]1[CH2:15][C:16]1[CH:27]=[CH:26][CH:25]=[CH:24][C:17]=12)=[O:12]

Participants

5

Reactant 1

HCID 58497898HCID 58497898, compound

Product 1

HCID 44538094HCID 44538094, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

10% Pd/C (0.10 g) is added to a solution of (2R,6R,11R)-trifluoro-methanesulfonic acid 3-[(S)-2,3-dihydro-benzo[1,4]dioxine-2-carbonyl]-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-8-yl ester (0.50 g) in methanol (15 mL) and ethyl acetate (25 mL). The resulting mixture is shaken under hydrogen atmosphere (50 psi) at room temperature overnight. Then, the catalyst is separated by filtration and the filtrate is concentrated under reduced pressure. The residue is purified by HPLC on reversed phase (MeCN/H2O) to give the product as a colorless gum-like solid.

Workup

  1. customThen, the catalyst is separated by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe residue is purified by HPLC on reversed phase (MeCN/H2O)

Sources & evidence

ORD record
ord-eeaaead711f741618cd5f7ce5fbe0101
Source dataset
uspto-grants-2015_07
Patent number
US09073870B2

Reaction notes

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