Tetrahydrofuran → HCID 11717334, compound

HRID 2275644Notes

Reaction equation

HRID 2275644 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([N:13]3[CH2:17][CH:16]([CH2:18][OH:19])[CH:15]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4O)[CH2:14]3)=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.O1CCCC1>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([N:13]3[CH2:14][CH:15]4[C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=5[O:19][CH2:18][CH:16]4[CH2:17]3)=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 11508998HCID 11508998, compound

Product 1

HCID 11717334HCID 11717334, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-[1-{[1-(4-chlorophenyl)cyclopropyl]carbonyl}-4-(hydroxymethyl)pyrrolidin-3-yl]phenol (13.0 mg, 0.0000350 mol), triphenylphosphine (20.0 mg, 0.0000762 mol) and diisopropyl azodicarboxylate (15.0 μL, 0.0000762 mol) in tetrahydrofuran (1.0 mL, 0.012 mol) was stirred at rt for 4 h. The mixture was diluted with methanol (0.80 mL) and the desired product from the mixture was isolated and purified by prep-HPLC. LCMS: m/z 354.5 (M+H)+

Sources & evidence

ORD record
ord-604251901f464a9796ca6070701eaf83
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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