HCID 66885811, compound → HCID 66884545, compound

HRID 2204054Notes

Reaction equation

HRID 2204054 reaction equation
[CH2:1]([O:4][C@H:5]1[C@H:10]([O:11][CH2:12][CH:13]=[CH2:14])[C@@H:9]([O:15][CH2:16][CH:17]=[CH2:18])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH3:35])=[CH:29][CH:28]=3)[CH:20]=2)[NH:7][C@@H:6]1[CH2:36][O:37][CH2:38][CH:39]=[CH2:40])[CH:2]=[CH2:3]>C1COCC1>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C@H:8]2[C@H:9]([O:15]/[CH:16]=[CH:17]/[CH3:18])[C@@H:10]([O:11]/[CH:12]=[CH:13]/[CH3:14])[C@H:5]([O:4]/[CH:1]=[CH:2]/[CH3:3])[C@@H:6]([CH2:36][O:37]/[CH:38]=[CH:39]/[CH3:40])[NH:7]2)=[CH:20][C:21]=1[CH2:26][C:27]1[CH:28]=[CH:29][C:30]([O:33][CH2:34][CH3:35])=[CH:31][CH:32]=1

Participants

3

Reactant 1

HCID 66885811HCID 66885811, compound

Product 1

HCID 66884545HCID 66884545, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ir(COD)[PCH3Ph2]PF6 (8 mg, 30 mol %) in THF (0.3 ml) was stirred under an atmosphere of H2 until the color changed from red to pale yellow (˜5 minutes). Compound from Step F (19 mg, 0.033 mol) in THF (0.5 ml) was then added and the mixture stirred at room temperature for 45 minutes and then concentrated. Purification by silica gel chromatography (20% EtOAc/hexanes) afforded (2S,3S,4R,5R,6R)-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-3,4,5-tris-[((E)-propenyl)oxy]-6-[((E)-propenyl)oxymethyl]-piperidine (15 mg, 0.026 mmol, 80%) as a colorless oil. MS (ES+) [M+H]+=568.

Workup

  1. customred to pale yellow (˜5 minutes)
  2. concentrationconcentrated
  3. customPurification by silica gel chromatography (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8779576dee09401f8326c759558dc8d4
Source dataset
uspto-grants-2016_06
Patent number
US09365602B2

Reaction notes

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