Triphenylphosphine → Methyl 12-cyclohexyl-3-hydroxy-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate

HRID 1012249Notes

Reaction equation

HRID 1012249 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][CH2:21][OH:22])[C:8]=2[C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][C:24]=2O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH:1]1([C:7]2[C:15]3[CH:14]=[CH:13][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][C:10]=3[N:9]3[C:8]=2[C:23]2[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][C:28]=2[O:22][CH2:21][CH2:20]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23152674methyl 3-cyclohexyl-2-(2,4-dihydroxyphenyl)-1-(2-hydroxyethyl)-1H-indole-6-carboxylate

Product 1

HCID 11994998Methyl 12-cyclohexyl-3-hydroxy-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylateYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-cyclohexyl-2-(2,4-dihydroxyphenyl)-1-(2-hydroxyethyl)-1H-indole-6-carboxylate (10.3 g, 28.2 mmol) in tetrahydrofuran (500 ml) were added triphenylphosphine (7.3 g, 27.7 mmol) and diethyl azodicarboxylate (4.4 ml, 27.7 mmol) under ice-cooling, and the mixture was stirred for 4 hr. The reaction mixture was concentrated and the obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=3:2) to give methyl 12-cyclohexyl-3-hydroxy-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate (6.5 g, yield 66%).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. customthe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-176d1ab98cf24cb8b9508ed75b6dc34a
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

Loading…