(R)-2-Amino-5-(3-pyridyl)pentane → (S,R*)-(E)-3-[2,2-bis(3-methoxyphenyl)-cyclopropyl]-N-[1-methyl-4-(3-pyridinyl)butyl]-2-propenamide

HRID 2232158Notes

Reaction equation

HRID 2232158 reaction equation
[N+](C1C=CC([O:10][C:11](=O)/[CH:12]=[CH:13]/[C@@H:14]2[CH2:16][C:15]2([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)=CC=1)([O-])=O.[CH3:34][C@@H:35]([NH2:45])[CH2:36][CH2:37][CH2:38][C:39]1[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=1>O1CCCC1>[CH3:32][O:31][C:27]1[CH:26]=[C:25]([C:15]2([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=3)[CH2:16][C@@H:14]2/[CH:13]=[CH:12]/[C:11]([NH:45][C@@H:35]([CH3:34])[CH2:36][CH2:37][CH2:38][C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)=[O:10])[CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 11062727(R)-2-Amino-5-(3-pyridyl)pentaneHCID 70374114(S)-(E)-3-[2,2-bis(3-methoxyphenyl)cyclopropyl]-2-propenoic acid 4-nitrophenyl ester

Product 1

HCID 86742538(S,R*)-(E)-3-[2,2-bis(3-methoxyphenyl)-cyclopropyl]-N-[1-methyl-4-(3-pyridinyl)butyl]-2-propenamideYield 60.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As in example 141, (S)-(E)-3-[2,2-bis(3-methoxyphenyl)cyclopropyl]-2-propenoic acid 4-nitrophenyl ester (2.2 g) was reacted with (R)-alpha-methyl-3-pyridinebutanamine (0.81 g) in tetrahydrofuran (15 mL) at ambient temperature overnight. The crude product, isolated in the usual manner, was purified by HPLC (ethyl acetate) and then crystallized from ethyl acetate-hexane to give 1.4 g of (S,R*)-(E)-3-[2,2-bis(3-methoxyphenyl)-cyclopropyl]-N-[1-methyl-4-(3-pyridinyl)butyl]-2-propenamide, mp 104°-106° C.

Workup

  1. customThe crude product, isolated in the usual manner
  2. customwas purified by HPLC (ethyl acetate)
  3. customcrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-52d96faf0f194649b89f0c28c0c36a3c
Source dataset
uspto-grants-1988_11
Patent number
US04786646

Reaction notes

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