Triphenylphosphine → HCID 68727290, compound

HRID 493174Notes

Reaction equation

HRID 493174 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]([C:11]2[O:12][C:13]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:14]=3[CH:15]=2)=[O:10])[CH2:3]1.[CH:21]([N:24]1[CH2:29][CH2:28][CH:27](O)[CH2:26][CH2:25]1)([CH3:23])[CH3:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]([C:11]2[O:12][C:13]3[CH:19]=[CH:18][C:17]([O:20][CH:27]4[CH2:28][CH2:29][N:24]([CH:21]([CH3:23])[CH3:22])[CH2:25][CH2:26]4)=[CH:16][C:14]=3[CH:15]=2)=[O:10])[CH2:3]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 796811-Isopropylpiperidin-4-olHCID 5363146Diisopropyl azodicarboxylateHCID 68726284HCID 68726284, compound

Product 1

HCID 68727290HCID 68727290, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The above prepared ((cis)-2,6-dimethyl-morpholin-4-yl)-(5-hydroxy-benzofuran-2-yl)-methanone (0.150 g, 0.545 mmol) was dissolved in 2.7 mL of THF and treated successively at 10° C. with 1-isopropyl-piperidin-4-ol (0.156 g, 2 eq.), triphenylphosphine (0.285 g, 2 eq.) and DIAD (0.212 mL, 2 eq.), and the mixture then kept at ambient temperature for another 3 h. Pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by two flash chromatographies (SiO2, NEt3/AcOEt=4/96 and CH2Cl2/MeOH=9/1), yielded eventually 0.140 g of the title compound as colorless oil.

Workup

  1. additionPouring
  2. extractionice/NH4Cl, twofold extraction with AcOEt
  3. washwashing with water
  4. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-f7391d1fdef64cba989f9d893c6666e6
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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