Triphenylphosphine → Methyl 2-[4-(4-fluorophenoxy)benzenesulfonyl]-6-(2-morpholin-4-ylethoxy)-1,2,3,4-tetrahydroisoquinoline-1-carboxylate

HRID 2265880Notes

Reaction equation

HRID 2265880 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[F:20][C:21]1[CH:51]=[CH:50][C:24]([O:25][C:26]2[CH:31]=[CH:30][C:29]([S:32]([N:35]3[CH2:44][CH2:43][C:42]4[C:37](=[CH:38][CH:39]=[C:40]([OH:45])[CH:41]=4)[CH:36]3[C:46]([O:48][CH3:49])=[O:47])(=[O:34])=[O:33])=[CH:28][CH:27]=2)=[CH:23][CH:22]=1.[N:52]1([CH2:58][CH2:59]O)[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[F:20][C:21]1[CH:22]=[CH:23][C:24]([O:25][C:26]2[CH:27]=[CH:28][C:29]([S:32]([N:35]3[CH2:44][CH2:43][C:42]4[C:37](=[CH:38][CH:39]=[C:40]([O:45][CH2:59][CH2:58][N:52]5[CH2:57][CH2:56][O:55][CH2:54][CH2:53]5)[CH:41]=4)[CH:36]3[C:46]([O:48][CH3:49])=[O:47])(=[O:33])=[O:34])=[CH:30][CH:31]=2)=[CH:50][CH:51]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 5462977Diethyl azodicarboxylateHCID 68679822Methyl 2-[4-(4-fluorophenoxy)benzenesulfonyl]-6-hydroxy-1,2,3,4-tetrahydro-isoquinoline-1-carboxylate

Product 1

HCID 68680877Methyl 2-[4-(4-fluorophenoxy)benzenesulfonyl]-6-(2-morpholin-4-ylethoxy)-1,2,3,4-tetrahydroisoquinoline-1-carboxylateYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

667 mg (2.0 mmol) of polymer-bound PPh3 (3 mmol/g) are introduced into 2 ml of THF and, at room temperature, 229 mg (0.5 mmol) of methyl 2-[4-(4-fluorophenoxy)-benzenesulfonyl]-6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate (3B), 242 μl (2.0 mmol) of 2-morpholin-4-ylethanol and 311 μl (2.0 mmol) of DEAD are added. After one hour, the mixture is filtered and the filtrate is concentrated in vacuo. The residue is chromatographed on silica gel (dichloromethane→dichloromethane/methanol 98:2), resulting in 53% of the title compound.

Workup

  1. filtrationthe mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe residue is chromatographed on silica gel (dichloromethane→dichloromethane/methanol 98:2)

Sources & evidence

ORD record
ord-b30bb2b706ba449197875fb5540bdb4d
Source dataset
uspto-grants-2010_12
Patent number
US07858619B2

Reaction notes

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