Tributylphosphine → HCID 57541940, compound

HRID 2422228Notes

Reaction equation

HRID 2422228 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[C@H:14]1(O)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15]1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>O1CCCC1.O>[C@@H:14]1([O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 6971243(R)-(-)-1-Indanol

Product 1

HCID 57541940HCID 57541940, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

Methyl 4-hydroxybenzenepropanoate (4.1 g, 22 mmol) was dissolved in tetrahydrofuran (50 mL) and the mixture was stirred at −30° C. (R)-1-Indanol (98% ee) (3.0 g, 22 mmol), 1,1′-(azodicarbonyl)dipiperidine (5.66 g, 22 mmol) and tributylphosphine (5.6 mL, 22 mmol) were added and the mixture was stirred at −30° C. for 23 hrs. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The mixture was concentrated under reduced pressure and the obtained oil was purified by silica gel chromatography (hexane to hexane/ethyl acetate=10:1) to give the title compound (4.4 g, yield 66%) as a yellow oil.

Workup

  1. additionwere added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationThe mixture was concentrated under reduced pressure
  6. customthe obtained oil was purified by silica gel chromatography (hexane to hexane/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-77ecfe1a9e0b483f892211abc6e755d5
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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