Triphenylphosphine → HCID 21939854, compound

HRID 1242878

Reaction equation

HRID 1242878 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH3:13][N:14]([CH2:16][CH:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([OH:27])[CH:23]=2)[CH2:18]1)[CH3:15].[CH3:28][O:29][C:30]1[CH:46]=[CH:45][C:33]([C:34]([O:36][C:37]2[CH:42]=[CH:41][C:40]([CH2:43]O)=[CH:39][CH:38]=2)=[O:35])=[CH:32][CH:31]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:15][N:14]([CH2:16][CH:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:27][CH2:43][C:40]3[CH:39]=[CH:38][C:37]([O:36][C:34]([C:33]4[CH:32]=[CH:31][C:30]([O:29][CH3:28])=[CH:46][CH:45]=4)=[O:35])=[CH:42][CH:41]=3)[CH:23]=2)[CH2:18]1)[CH3:13]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 219397642-(N,N-Dimethylamino)methyl-6-hydroxytetralinHCID 219400704-(Hydroxymethyl)phenyl 4-methoxybenzoate

Product 1

HCID 21939854HCID 21939854, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (40% toluene solution, 950 mg) was added dropwise to THF solution (3 ml) of 2-[(N,N-dimethylamino)methyl]-6-hydroxytetralin (150 mg), 4-(hydroxymethyl)phenyl 4-methoxybenzoate (570 mg) and triphenylphosphine (574 mg) at room temperature, which was stirred for 3 hours. The reaction mixture was concentrated, and the residue was purified using alumina column chromatography (development solvent; hexane˜hexane:ethyl acetate=6:1), and recrystallized (ethyl acetate-hexane) to give the titled compound (175 mg).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified
  3. customrecrystallized (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-3bb54d2b3b8547e8adcb154f5c2e16b6
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Linked notes

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