Cyclopentanol → HCID 11653712, compound

HRID 557936Notes

Reaction equation

HRID 557936 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-a65ee549daf04a1ea6f4c2d247fc0394
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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