Isopropanol → HCID 59314341, compound

HRID 1047942Notes

Reaction equation

HRID 1047942 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2[OH:24])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2].[CH3:25][CH:26](O)[CH3:27].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>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2[O:24][CH:26]([CH3:27])[CH3:25])[CH2:7][C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 11776Triphenylphosphine2×HCID 5363146Diisopropyl azodicarboxylateHCID 59314142HCID 59314142, compound

Product 1

HCID 59314341HCID 59314341, compoundYield 180.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 100 mL round bottom flask containing the 2-(2-hydroxy-3-methyl-benzylamino)-indan-2-carboxylic acid ethyl ester (364, 1.01 g, 3.10 mmol) is charged with dry tetrahydrofuran (THF, 10 mL). A stirring bar is added and stirring is initiated. After dissolution, iPrOH ([67-63-0], 0.47 mL, 6.21 mmol) and triphenylphosphine ([603-35-0], 1.63 g, 6.21 mmol) are added in turn. After dissolution of the triphenylphosphine, diisopropylazodicarboxylate (1.20 mL, 6.21 mmol) is added. The reaction flask is capped and allowed to stir at ambient temperature overnight. After 24 h, tlc analysis (silica, 1:2 EtOAc/Heptanes) indicates that the starting material is completely consumed and converted to a higher moving spot as visualized by UV. The stirring bar is removed from the reaction flask and the solvent removed under reduced pressure. Pumping to constant weight gives 2.06 g of viscous yellow oil. This is dissolved in DCM (10 mL) and applied to an ISCO Companion which had been fitted with a 40 g column (silica). The column is eluted with EtOAc/heptanes (5%) for 4 column volumes followed by a linear gradient to 60% EtOAc/heptanes over 10 column volumes and then 90% EtOAc/heptanes for 2 column volumes. 17 mL fractions of UV Active eluent are collected. Fractions 5-14 are combined and evaporated by pumping to constant weight to give viscous residue (0.42 g, 37%).

Workup

  1. additionA stirring bar is added
  2. additionare added in turn
  3. additionis added
  4. customThe reaction flask is capped
  5. stirringto stir at ambient temperature overnight
  6. customis completely consumed
  7. customThe stirring bar is removed from the reaction flask
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-44cb0896bdcc407c930f11f1bf12a9a0
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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