3-(1-Benzyloxycarbonylpyrrolidin-2(R)-ylmethyl)-5-(3-carbamoylphenyl)-1H-indole → 5-(3-Carbamoylphenyl)-3-(pyrrolidin-2(R)-ylmethyl)-1H-indole

HRID 1441059Notes

Reaction equation

HRID 1441059 reaction equation
C(OC([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]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32](=[O:34])[NH2:33])[CH:27]=3)[CH:24]=2)[NH:19][CH:18]=1)=O)C1C=CC=CC=1>C(O)C>[C:32]([C:28]1[CH:27]=[C:26]([C:23]2[CH:24]=[C:25]3[C:20](=[CH:21][CH:22]=2)[NH:19][CH:18]=[C:17]3[CH2:16][C@H:12]2[CH2:13][CH2:14][CH2:15][NH:11]2)[CH:31]=[CH:30][CH:29]=1)(=[O:34])[NH2:33]

Participants

3

Reactant 1

HCID 228595563-(1-Benzyloxycarbonylpyrrolidin-2(R)-ylmethyl)-5-(3-carbamoylphenyl)-1H-indole

Product 1

HCID 228595705-(3-Carbamoylphenyl)-3-(pyrrolidin-2(R)-ylmethyl)-1H-indoleYield 77.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(1-Benzyloxycarbonylpyrrolidin-2(R)-ylmethyl)-5-(3-carbamoylphenyl)-1H-indole (700 mg, 1.391 mmol) (see Preparation 40) in ethanol was reduced using catalytic hydrogenation, as described in Example 35. This gave the title compound as a white foam (345 mg). Found: C,71.16; H,6.98; N,12.34; C20H21N3O.H2O requires: C,71.19; H,6.87; N, 12.45.

Sources & evidence

ORD record
ord-e26eb76220774fd7940ee61062e1fbe2
Source dataset
uspto-grants-1996_03
Patent number
US05502065

Reaction notes

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