Triethylamine → 2-(((3R,4R)-4-(Allyloxy)-1-benzylpyrrolidin-3-yl)methyl)-6-(2,5-dimethyl-1H-pyrrol-1-yl)-4-methylpyridine

HRID 73488Notes

Reaction equation

HRID 73488 reaction equation
[CH2:1]([O:4][C@@H:5]([CH2:24][NH:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C@H:6]([CH2:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([N:17]2[C:21]([CH3:22])=[CH:20][CH:19]=[C:18]2[CH3:23])[N:11]=1)[CH2:7]O)[CH:2]=[CH2:3].CS(Cl)(=O)=O.C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([O:4][C@H:5]1[CH2:24][N:25]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:7][C@H:6]1[CH2:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([N:17]2[C:18]([CH3:23])=[CH:19][CH:20]=[C:21]2[CH3:22])[N:11]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 44543306(2R,3R)-3-(Allyloxy)-4-(benzylamino)-2-((6-(2,5-dimethyl-1H-pyrrol-1-yl)-4-methylpyridin-2-yl)methyl)butan-1-ol

Product 1

HCID 445433072-(((3R,4R)-4-(Allyloxy)-1-benzylpyrrolidin-3-yl)methyl)-6-(2,5-dimethyl-1H-pyrrol-1-yl)-4-methylpyridineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 20 (70 mg, 0.16 mmol) in CH2Cl2 (2.0 mL) at room temperature was added MsCl (15 μL, 0.19 mmol). After 2 min, triethylamine (34 μL, 0.24 mmol) was added dropwise as a solution in CH2Cl2 (340 μL). The reaction was allowed to stir for another 2 min and concentrated by rotary evaporation. The crude material was purified by flash column chromatography (EtOAc:hexanes, 2:1-4:1) to give 2 (66 mg, 0.16 mmol, 100%) as a colorless oil: 1H NMR (500 MHz, CDCl3) δ 2.12 (s, 6H), 2.38 (s, 3H), 2.38-2.43 (m, 1H), 2.53-2.56 (dd, J=3.0, 10.0 Hz, 1H), 2.77-2.80 (dd, J=7.5, 8.0 Hz, 1H), 2.80-2.91 (m, 2H), 3.08-3.13 (m, 2H), 3.79-3.83 (dd, J=5.5, 13.0 Hz, 1H), 3.97-3.99 (br s, 2H), 5.14-5.16 (dd, J=1.0, 10.0 Hz, 1H), 5.23-5.26 (dd, J=1.0, 17.0 Hz, 1H), 5.80-5.89 (m, 1H), 5.89 (s, 2H), 6.84 (s, 1H), 7.00 (s, 1H), 7.20-7.40 (m, 5H); 13C NMR (125 MHz, CDCl3) δ 13.5, 21.2, 36.2, 42.5, 58.4, 60.2, 61.0, 70.9, 79.1, 98.9, 106.8, 116.7, 120.1, 123.4, 127.1, 128.5, 128.7, 128.9, 135.2, 149.4, 151.8, 161.3; LCQ-MS (M+H+) calcd for C27H34N3O 416. found 416; LC-TOF-MS (M+H+) calcd for C27H34N3O 416.27019. found 416.26956.

Workup

  1. concentrationconcentrated by rotary evaporation
  2. customThe crude material was purified by flash column chromatography (EtOAc:hexanes, 2:1-4:1)

Sources & evidence

ORD record
ord-573ac42c32b74f318b7c60a631448a83
Source dataset
uspto-grants-2014_09
Patent number
US08829187B1

Reaction notes

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