Water → 6-{4-[(1R,2S)-2-(2-hydroxyethyl)cyclopropyl]piperidin-1-yl}pyridine-3-carbaldehyde

HRID 1474733Notes

Reaction equation

HRID 1474733 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][CH:13]([C@H:16]2[CH2:18][C@H:17]2[CH2:19][CH2:20][OH:21])[CH2:12][CH2:11]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[OH:21][CH2:20][CH2:19][C@@H:17]1[CH2:18][C@@H:16]1[CH:13]1[CH2:12][CH2:11][N:10]([C:2]2[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][CH:3]=2)[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27640536-Chloropyridine-3-carbaldehydeHCID 867111782-((1S,2R)-2-(piperidin-4-yl)cyclopropyl)ethanol

Product 1

HCID 1176784086-{4-[(1R,2S)-2-(2-hydroxyethyl)cyclopropyl]piperidin-1-yl}pyridine-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 250 ml RBF the 6-chloropyridine-3-carbaldehyde (1.907 g, 13.47 mmol) and 2-[(1S,2R)-2-(piperidin-4-yl)cyclopropyl]ethanol (2.28 g, 13.47 mmol) were dissolved in DMF (13.47 ml). Cesium carbonate (13.17 g, 40.4 mmol) was added and the mixture stirred at RT overnight. The mixture was poured into 4:1 water:brine (200 ml), extracted with EtOAc (3×100 ml), the organic fractions combined, washed with brine, dried over Na2SO4, filtered and the volatiles removed in vacuo. The residue was purified by column chromatography on silica gel, Biotage 100M, using a gradient eluant of 0-100% EtOAc/hexanes to afford the title compound. LC/MS (m/z): 275 (M+H)+.

Workup

  1. extractionbrine (200 ml), extracted with EtOAc (3×100 ml)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe volatiles removed in vacuo
  6. customThe residue was purified by column chromatography on silica gel, Biotage 100M

Sources & evidence

ORD record
ord-612961ff4e5645eeb2bfbaf40df569ae
Source dataset
uspto-grants-2015_04
Patent number
US09018224B2

Reaction notes

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