Cyclopentanol → HCID 11653712, compound

HRID 969200Notes

Reaction equation

HRID 969200 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3([C:17]4[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=4)[CH2:16][CH2:15]3)=[O:13])[CH2:8]2)[CH:2]=1.[CH:24]1(O)[CH2:28][CH2:27][CH2:26][CH2:25]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH:24]1([O:23][C:20]2[CH:19]=[CH:18][C:17]([C:14]3([C:12]([N:9]4[CH2:10][CH2:11][CH:7]([C:3]5[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=5)[CH2:8]4)=[O:13])[CH2:16][CH2:15]3)=[CH:22][CH:21]=2)[CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 7298CyclopentanolHCID 11776TriphenylphosphineHCID 66662125HCID 66662125, compound

Product 1

HCID 11653712HCID 11653712, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-{1-[(3-pyridin-3-ylpyrrolidin-1-yl)carbonyl]cyclopropyl}phenol (40.0 mg, 0.000130 mol) in tetrahydrofuran were added cyclopentanol (29.4 μL, 0.000324 mol) diethyl azodicarboxylate (0.0511 mL, 0.000324 mol), and triphenylphosphine (85.0 mg, 0.000324 mol) at room temperature, and the reaction mixture was stirred overnight. The crude product was purified by prep-HPLC. LCMS: m/z 377.1 (M+H)+

Workup

  1. customThe crude product was purified by prep-HPLC

Sources & evidence

ORD record
ord-3b15f85e8e644000ab98e069c2d74995
Source dataset
uspto-grants-2007_12
Patent number
US07304081B2

Reaction notes

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