HCID 11323701, compound → 6-(5-{[(2S)-1-Methylpyrrolidin-2-yl]methoxy}pyridin-3-yl)hexan-1-ol

HRID 1660725Notes

Reaction equation

HRID 1660725 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[C:7][C:8]1[CH:9]=[C:10]([O:14][CH2:15][C@@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[CH3:21])[CH:11]=[N:12][CH:13]=1>[Pd].CCOC(C)=O>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:9]=[C:10]([O:14][CH2:15][C@@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[CH3:21])[CH:11]=[N:12][CH:13]=1

Participants

4

Reactant 1

HCID 11323701HCID 11323701, compound

Product 1

HCID 593305466-(5-{[(2S)-1-Methylpyrrolidin-2-yl]methoxy}pyridin-3-yl)hexan-1-olYield 100.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-(6-hydroxy-1-hexynyl)-3-(1-methyl-2(S) -pyrrolidinylmethoxy)pyridine (50 mg, 0.17 mmol), 10% Pd—C (10 mg), and EtOAc (5 mL) was stirred under H2 (1 atm) at room temperature for 3 h. The reaction mixture was filtered through Celite and washed with MeOH. The filtrate was concentrated to provide an oil (50 mg, 99%), [α]D−31 (c 1.6, CHCl3). 1H NMR (CDCl3) δ 8.12 (d, 1H, J=2.4 Hz), 8.03 (d, 1H, J=1.5 Hz), 7.03 (t, 1H, J=2.1 Hz), 4.02 (dd, 1H, J=9.3, 5.4 Hz), 3.92 (dd, 1H, J=9.3, 5.4 Hz), 3.62 (t, 2H, J=6.6 Hz), 3.16-3.09 (m, 1H), 2.72-2.63 (m, 1H), 2.58 (t, 2H, J=7.5 Hz), 2.48 (s, 3H), 2.50 (br s, 1H), 2.31 (td, 1H, J=9.3, 7.5 Hz), 2.10-1.97 (m, 1H), 1.93-1.28 (m, 11H); 13C NMR (CDCl3) δ 155.02, 142.17, 138.54, 134.89, 121.29, 70.93, 64.13, 62.48, 57.67, 41.67, 32.64, 32.58, 30.86, 28.79, 28.48, 25.48, 22.94.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed with MeOH
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8c3a920279a24266984ca2e0691ae6d9
Source dataset
uspto-grants-2011_10
Patent number
US08030300B2

Reaction notes

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