Vinylcyclopentanol → 3-(N-Benzyloxycarbonyl-2(R)-pyrrolidinylmethyl)-5-[2-(1-hydroxycyclopentyl)ethenyl]-1H-indole

HRID 975140Notes

Reaction equation

HRID 975140 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23](Br)[CH:24]=2)[NH:19][CH:18]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:27]([C:29]1([OH:34])[CH2:33][CH2:32][CH2:31][CH2:30]1)=[CH2:28]>CO>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([CH:28]=[CH:27][C:29]3([OH:34])[CH2:33][CH2:32][CH2:31][CH2:30]3)[CH:24]=2)[NH:19][CH:18]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 317028VinylcyclopentanolHCID 22859561(R)-Benzyl 2-((5-bromo-1H-indol-3-yl)methyl)pyrrolidine-1-carboxylate

Product 1

HCID 543222443-(N-Benzyloxycarbonyl-2(R)-pyrrolidinylmethyl)-5-[2-(1-hydroxycyclopentyl)ethenyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Obtained by a procedure similar to that described in Example 1, from 3-(N-benzyloxycarbonyl-2(R)-pyrrolidinylmethyl)-5-bromo-1H-indole (Preparation 1) and 1-vinylcyclopentanol (Example 5(a)), as a foam. Rf 0.40 (SS 10). [α]D25 -31° (c=0.1, CH3OH). Found: C,75.58; H,7.24; N,6.22. C28H32N2O3 requires C,75.64; H,7.26; N,6.30%.

Workup

  1. customObtained by a procedure similar to

Sources & evidence

ORD record
ord-090cfc89f43d452cb40f727f8e37e3bb
Source dataset
uspto-grants-1997_03
Patent number
US05607960

Reaction notes

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