Chlorine → Rac.-4-[2-(n-tert-butoxycarbonylaminomethyl)pyrrolidin-1-ylcarbonyl]-3-chlorobenzonitrile

HRID 2053768Notes

Reaction equation

HRID 2053768 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C.[C:44]([O:48][C:49]([NH:51][CH2:52][CH:53]1[CH2:57][CH2:56][CH2:55][NH:54]1)=[O:50])([CH3:47])([CH3:46])[CH3:45].ClCl>O1CCCC1.ClCCl.C(O)C>[C:44]([O:48][C:49]([NH:51][CH2:52][CH:53]1[CH2:57][CH2:56][CH2:55][N:54]1[C:4]([C:3]1[CH:7]=[CH:8][C:9]([C:11]#[N:12])=[CH:10][C:2]=1[Cl:1])=[O:6])=[O:50])([CH3:47])([CH3:45])[CH3:46]

Participants

8

Reactant 5

HCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2318942-Chloro-4-cyanobenzoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21834643Pyrrolidin-2-ylmethyl-carbamic acid tert-butyl ester

Product 1

HCID 69309927Rac.-4-[2-(n-tert-butoxycarbonylaminomethyl)pyrrolidin-1-ylcarbonyl]-3-chlorobenzonitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example I d from 2-chloro-4-cyanobenzoic acid, TBTU, N,N-diisopropylethylamine, and rac.-2-(N-tert-butoxycarbonylaminomethyl)pyrrolidine in tetrahydrofuran. Yield: quantitative; Rf value: 0.52 (silica gel; dichloromethane/ethanol=95:5); C18H22ClN3O3 (363.85); mass spectrum: (M+H)+=364/366 (chlorine isotope).

Workup

  1. customPrepared analogously to Example I

Sources & evidence

ORD record
ord-a9ef35e75e844e53ba3a0fe13fae0666
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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