Morpholine → HCID 71075220, compound

HRID 2170707Notes

Reaction equation

HRID 2170707 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C@@H:4]([O:6][C:7]1[CH:8]=[C:9]([CH:28]=[CH:29][CH:30]=1)[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([C:20]([O:22]CC=C)=[O:21])=[CH:17][CH:18]=2)[C:13]([CH3:26])=[C:12]1[CH3:27])[CH3:5].N1CCOCC1>C1COCC1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:31])[C@@H:4]([O:6][C:7]1[CH:8]=[C:9]([CH:28]=[CH:29][CH:30]=1)[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH:18]=2)[C:13]([CH3:26])=[C:12]1[CH3:27])[CH3:5]

Participants

6

Reactant 2

HCID 8083MorpholineHCID 86674594HCID 86674594, compound

Product 1

HCID 71075220HCID 71075220, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (S)-allyl 1-(3-((1-methoxy-1-oxopropan-2-yl)oxy)benzyl)-2,3-dimethyl-1H-indole-5-carboxylate (1.0 g, 2.37 mmol, 1 equiv), Pd(PPh3)4 (277 mg, 0.24 mmol, 0.1 equiv), and morpholine (2 mL, 23.7 mmol, 10 equiv) in anhydrous THF (30 mL) was stirred at room temperature under argon atmosphere for 16 h. The completion of the reaction was monitored by anal. HPLC. The crude mixture was dissolved in AcOEt (100 mL) and washed with a 0.5N HCl aqueous solution (×2) and brine, then dried over Na2SO4. The filtrate was concentrated to obtain the crude product which was purified by flash chromatography (AcOEt/Hexane 0->60%) to obtain the title compound.

Workup

  1. washwashed with a 0.5N HCl aqueous solution (×2) and brine
  2. dry with materialdried over Na2SO4
  3. concentrationThe filtrate was concentrated
  4. customto obtain the crude product which
  5. customwas purified by flash chromatography (AcOEt/Hexane 0->60%)

Sources & evidence

ORD record
ord-8c5d03b92a3349aca69290d7e21ac224
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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