Triphenylphosphine → HCID 10146789, compound

HRID 2269901Notes

Reaction equation

HRID 2269901 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:38]=[C:39]([O:43][CH3:44])[C:40]=1[O:41][CH3:42])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH:24]([C:27]([C:29]3[NH:33][C:32]4[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=4[N:30]=3)=[O:28])[CH2:23][CH2:22]2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9]1)=[O:7].[CH3:45][C:46]([CH3:53])=[CH:47][CH2:48][O:49][CH2:50][CH2:51]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.CO.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:38]=[C:39]([O:43][CH3:44])[C:40]=1[O:41][CH3:42])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH:24]([C:27]([C:29]3[N:30]([CH2:51][CH2:50][O:49][CH2:48][CH:47]=[C:46]([CH3:53])[CH3:45])[C:31]4[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=4[N:33]=3)=[O:28])[CH2:23][CH2:22]2)([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:9]1)=[O:7]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 101213901-(3,4,5-trimethoxy-benzoyl)-3-[2-[4-[1H-benzoimidazole-2-carbonyl]-piperidin-1-yl]-ethyl]-3-phenyl-pyrrolidineHCID 18333454Poly(oxy-1,2-ethanediyl), α-(3-methyl-2-buten-1-yl)-ω-hydroxy-

Product 1

HCID 10146789HCID 10146789, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

Combine 1-(3,4,5-trimethoxy-benzoyl)-3-[2-[4-[1H-benzoimidazole-2-carbonyl]-piperidin-1-yl]-ethyl]-3-phenyl-pyrrolidine (0.62 g, 1.0 mmol), and 2-(3,3-dimethylallyloxy)-ethanol (0.14 g, 1.0 mmol), triphenylphosphine (0.33 g, 1.27 mmol) in tetrahydrofuran (2 mL). Add dropwise diethyl azodicarboxylate ((0.2 mL, 1.27.mmol). After 18 hours, evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 10% methanol/ethyl acetate to give the title compound: Rf=0.35 (silica gel, 10% methanol/ethyl acetate).

Workup

  1. customevaporate in vacuo
  2. customto give a residue

Sources & evidence

ORD record
ord-9b94b70539c9443f9eaba7de0ddb21f5
Source dataset
uspto-grants-2001_12
Patent number
US06329392B1

Reaction notes

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