Triphenylphosphine → methyl (S)-8-[2-[6-(methylamino)pyridin-2-yl]ethoxy]-3-oxo-2-(2-phenylethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate

HRID 2416746Notes

Reaction equation

HRID 2416746 reaction equation
N(C(OC(C)C)=O)=N[C:3](OC(C)C)=O.[OH:15][C:16]1[CH:39]=[CH:38][C:19]2[CH2:20][C@@H:21]([CH2:34][C:35]([O-:37])=[O:36])[C:22](=[O:33])[N:23]([CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:24][C:18]=2[CH:17]=1.[CH3:40][NH:41][C:42]1[N:47]=[C:46]([CH:48](O)[CH3:49])[CH:45]=[CH:44][CH:43]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:40][NH:41][C:42]1[N:47]=[C:46]([CH2:48][CH2:49][O:15][C:16]2[CH:39]=[CH:38][C:19]3[CH2:20][C@@H:21]([CH2:34][C:35]([O:37][CH3:3])=[O:36])[C:22](=[O:33])[N:23]([CH2:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:24][C:18]=3[CH:17]=2)[CH:45]=[CH:44][CH:43]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 223194656-(Methylamino)-2-pyridylethanolHCID 57459735(S)-8-hydroxy-3-oxo-2-(2-phenylethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate

Product 1

HCID 57217922methyl (S)-8-[2-[6-(methylamino)pyridin-2-yl]ethoxy]-3-oxo-2-(2-phenylethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetateYield 51.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (0.3 mL, 1.5 mmole) was added to a solution of (S)-8-hydroxy-3-oxo-2-(2-phenylethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate (350 mg, 1.0 mmole), 6-(methylamino)-2-pyridylethanol (228 mg, 1.5 mmole), and triphenylphosphine (393 mg, 1.5 mmole) in anhydrous THF (10 mL) at 0° C. The mixture was allowed to warm to RT over 72 hr then was concentrated. Flash silica gel chromatography (50% EtOAc/hexanes) followed by a second flash silica gel chromatography (25% EtOAc/hexanes) gave the title compound as a white foam (250 mg, 51%): MS (ES) m/e 488 (M+H)+.

Workup

  1. concentrationthen was concentrated

Sources & evidence

ORD record
ord-c6fe0f84bdb343019b2caae103c042d1
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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