1-(1-Naphthoyl)-3-(R)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(S)-(cyclopropyl)pyrrolidine → 1-(n-(3-t-Butoxycarbonylaminopropyl)-7-indolecarbonyl)-3-(r)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(s)-(cyclopropyl)pyrrolidine

HRID 279226Notes

Reaction equation

HRID 279226 reaction equation
[C:1]1([C:11]([N:13]2[CH2:17][C@@H:16]([CH:18]3[CH2:20][CH2:19]3)[C@H:15]([CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[CH2:14]2)=[O:12])[C:10]2[C:5](=[CH:6]C=CC=2)[CH:4]=[CH:3][CH:2]=1.C(C1C=CC=C2C=1[N:45]([CH2:47][CH2:48][CH2:49][NH:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH:44]=C2)(O)=O>>[C:54]([O:53][C:51]([NH:50][CH2:49][CH2:48][CH2:47][N:45]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][C:1]=2[C:11]([N:13]2[CH2:17][C@@H:16]([CH:18]3[CH2:20][CH2:19]3)[C@H:15]([CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[CH2:14]2)=[O:12])[CH:6]=[CH:44]1)=[O:52])([CH3:57])([CH3:56])[CH3:55]

Participants

3

Reactant 2

HCID 187135061-(1-Naphthoyl)-3-(R)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(S)-(cyclopropyl)pyrrolidineHCID 701637397-carboxy-N-(3-t-butoxycabonylaminopropyl)indole

Product 1

HCID 187135271-(n-(3-t-Butoxycarbonylaminopropyl)-7-indolecarbonyl)-3-(r)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(s)-(cyclopropyl)pyrrolidineYield 5.4%

Procedure

1-(N-(3-t-butoxycarbonylaminopropyl)-7-indolecarbonyl)-3-(R)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(S)-(cyclopropyl)pyrrolidine (0.13 g) was prepared from 0.125 g (4 mmol) of 3-(S)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(S)-(cyclopropyl)pyrrolidine (Example 9) and 0.13 g (4.3 mmol) of 7-carboxy-N-(3-t-butoxycabonylaminopropyl)indole as described in Example 11. It was purified by chromatography (silica, acetone:hexanes, 3:7).

Workup

  1. customIt was purified by chromatography (silica, acetone:hexanes, 3:7)

Sources & evidence

ORD record
ord-f4f8b3de05bb4899b5f89c96aa0f7b32
Source dataset
uspto-grants-2002_03
Patent number
US06362201B1

Reaction notes

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