Triphenylphosphine → HCID 18186393, compound

HRID 1180200Notes

Reaction equation

HRID 1180200 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:14]=3)[CH:9]2[CH2:26][C:27]2[CH:32]=[CH:31][C:30](/[CH:33]=[CH:34]/[C:35]([NH:37][CH2:38][CH2:39][OH:40])=O)=[CH:29][CH:28]=2)=[CH:4][CH:3]=1.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[O:40]1[CH2:39][CH2:38][N:37]=[C:35]1/[CH:34]=[CH:33]/[C:30]1[CH:29]=[CH:28][C:27]([CH2:26][CH:9]2[C:10]3[C:15](=[CH:14][C:13]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:12][CH:11]=3)[CH2:16][CH2:17][N:8]2[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18186404HCID 18186404, compound

Product 1

HCID 18186393HCID 18186393, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2E)-3-(4-{[2-(4-fluorophenyl)-6-(phenylmethoxy)(1,2,3,4-tetrahydroisoquinolyl)]methyl}phenyl)-N-(2-hydroxyethyl)prop-2-enamide (0.32 g, 0.6 mmol) and diethyl azodicarboxylate (0.136 g, 0.78 mmol) in tetrahydrofuran (10 mL) was added dropwise a solution of triphenylphosphine (0.205 g, 0.78 mmol) in tetrahydrofuran (2 mL). After it was stirred at room temperature for 2 hours, the solvent was evaporated. The residue was then purified by chromatography (SiO2, 50% ethyl acetate/hexane) to provide the title compound (0.267 g, 86% yield): 1H NMR (CDCl3) 7.29-7.44 (m, 9H), 7.01 (d, 2H), 6.92 (m, 2H), 6.69-6.76 (m, 5H), 6.60 (d, 1H), 5.03 (s, 2H), 4.75 (t, 1H), 4.35 (t, 2H), 3.99 (t, 2H), 3.56 (m, 1H), 3.50 (m, 1H), 3.16 (dd, 1H), 2.95 (m, 2H), 2.67 (dt, 1H); ES-MS m/z 519 [M+H]+.

Workup

  1. customthe solvent was evaporated
  2. customThe residue was then purified by chromatography (SiO2, 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-68fcffeff661459d8a13201f3f071e9a
Source dataset
uspto-grants-2007_10
Patent number
US07279489B2

Reaction notes

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