Aluminium lithium hydride → HCID 67322682, compound

HRID 1846626Notes

Reaction equation

HRID 1846626 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[C:23]([NH:24][C:25](=[O:33])[C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=3)=[CH:22][C:21]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:20][N:19]=2)[CH2:14][CH2:13]1)C>O1CCCC1>[Cl:32][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][CH:29]=1)[C:25]([NH:24][C:23]1[C:18]([N:15]2[CH2:14][CH2:13][CH:12]([CH2:11][CH2:10][OH:9])[CH2:17][CH2:16]2)=[N:19][CH:20]=[C:21]([S:34]([CH3:37])(=[O:36])=[O:35])[CH:22]=1)=[O:33]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68303804HCID 68303804, compound

Product 1

HCID 67322682HCID 67322682, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of 0.202 g (5.32 mmol) of lithium aluminum hydride in dry tetrahydrofuran (2 mL), cooled to 0° C., is added 1.70 g (3.54 mmol) of [3′-(3-chloro-benzoylamino)-5′-methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-acetic acid ethyl ester as a solution in tetrahydrofuran (6 mL). The mixture is warmed to room temperature and stirred for 1 hour then cooled in an ice bath. Excess reactants are consumed by the dropwise addition of water (0.2 mL) followed by a 15% NaOH solution (0.2 mL) and additional water (0.4 mL). The mixture is stirred at room temperature for 30 minutes then filtered through a pad of diatomaceous earth. The filter pad is washed with tetrahydrofuran and the combined filtrate is concentrated under reduced pressure. The residue is purified by flash chromatography on neutral alumina to yield 1.3 g (86%) of 3-chloro-N-[4-(2-hydroxy-ethyl)-5′-methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-3′-yl]-benzamide.

Workup

  1. temperatureThe mixture is warmed to room temperature
  2. temperaturethen cooled in an ice bath
  3. customExcess reactants are consumed by the dropwise addition of water (0.2 mL)
  4. stirringThe mixture is stirred at room temperature for 30 minutes
  5. filtrationthen filtered through a pad of diatomaceous earth
  6. washThe filter pad is washed with tetrahydrofuran
  7. concentrationthe combined filtrate is concentrated under reduced pressure
  8. customThe residue is purified by flash chromatography on neutral alumina

Sources & evidence

ORD record
ord-18f764aef4a94c88aafe9084d9968d8c
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

Loading…