Methyl vinyl ketone → 3-(N-Benzyloxycarbonyl-2(R)-pyrrolidinylmethyl)-5-(3-oxo-1-but-1-enyl)-1H-indole

HRID 975141Notes

Reaction equation

HRID 975141 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]([CH3:31])=[O:30])=[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](=[O: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 6570Methyl vinyl ketoneHCID 22859561(R)-Benzyl 2-((5-bromo-1H-indol-3-yl)methyl)pyrrolidine-1-carboxylate

Product 1

HCID 544046923-(N-Benzyloxycarbonyl-2(R)-pyrrolidinylmethyl)-5-(3-oxo-1-but-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 methyl vinyl ketone, as a foam. Rf 0.60 (SS 7). [α]D25 -51° (c=0.1, CH3OH). Found: C,74.16; H,6.39; N,6.92. C25H26N2O3 requires C,74.60; H,6.51; N,6.96%.

Workup

  1. customObtained by a procedure similar to

Sources & evidence

ORD record
ord-951a8f598b36474fbe8f5a30543781e6
Source dataset
uspto-grants-1997_03
Patent number
US05607960

Reaction notes

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