3-Ethyl-1-penten-3-ol → 3-(N-Benzyloxycarbonyl-2(R)-pyrrolidinylmethyl)-5-(3-ethyl-3-hydroxy-1-pent-1-enyl)-1H-indole

HRID 975143Notes

Reaction equation

HRID 975143 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.[CH2:27]([C:29]([OH:34])([CH2:32][CH3:33])[CH:30]=[CH2:31])[CH3:28]>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]([CH2:32][CH3:33])([OH:34])[CH2:30][CH3:31])[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 1205133-Ethyl-1-penten-3-olHCID 22859561(R)-Benzyl 2-((5-bromo-1H-indol-3-yl)methyl)pyrrolidine-1-carboxylate

Product 1

HCID 536712503-(N-Benzyloxycarbonyl-2(R)-pyrrolidinylmethyl)-5-(3-ethyl-3-hydroxy-1-pent-1-enyl)-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 3-ethylpent-1-en-3-ol (Example 9(a)), as a foam. Rf 0.66 (SS 7). [α]D25 -27° (c=0.1, CH3OH). Found: C,75.33; H,+.29; N,5.65. C28H34N2O3 requires C,75.30; H,7.67; N,6.26%.

Workup

  1. customObtained by a procedure similar to

Sources & evidence

ORD record
ord-6eae00ee7993437abc540579c09ea6d8
Source dataset
uspto-grants-1997_03
Patent number
US05607960

Reaction notes

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