Triphenylphosphine → HCID 68565539, compound

HRID 1786465Notes

Reaction equation

HRID 1786465 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([OH:15])=[C:10]([CH3:16])[CH:9]=2)=[O:5])[CH3:2].[CH:17]([N:20]1[CH2:25][CH2:24][CH:23](O)[CH2:22][CH2:21]1)([CH3:19])[CH3:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH:23]1[CH2:24][CH2:25][N:20]([CH:17]([CH3:19])[CH3:18])[CH2:21][CH2:22]1)=[C:10]([CH3:16])[CH:9]=2)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 796811-Isopropylpiperidin-4-olHCID 97268Di-tert-butyl azodicarboxylateHCID 68564618HCID 68564618, compound

Product 1

HCID 68565539HCID 68565539, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 0.125 g (0.57 mmol) 5-hydroxy-6-methyl-1H-indole-2-carboxylic acid ethyl ester in 3 mL tetrahydrofuran, 98 mg (0.68 mmol) 1-isopropyl-piperidin-4-ol and 0.18 g (0.68 mmol) triphenylphosphine were added. The reaction was cooled to 0° C., 0.16 g (0.68 mmol) di-tert-butyl azodicarboxylate were added and the cooling bath was removed. After stirring 18 h at room temperature the volatile components were evaporated and the residue was purified by flash chromatography on silica gel using a gradient of dichloromethane:methanol (100:0 to 50:50 v/v) as eluant, to afford 74 mg (38%) of the title compound as a light-yellow foam.

Workup

  1. additionwere added
  2. customthe cooling bath was removed
  3. customwere evaporated
  4. customthe residue was purified by flash chromatography on silica gel using a gradient of dichloromethane:methanol (100:0 to 50:50 v/v) as eluant

Sources & evidence

ORD record
ord-bdc9eaeae824466c8063ebed2b0bdb5d
Source dataset
uspto-grants-2009_03
Patent number
US07507736B2

Reaction notes

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