Aluminium lithium hydride → HCID 58243390, compound

HRID 2361695Notes

Reaction equation

HRID 2361695 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1([N:11]2[CH2:17][CH2:16][CH2:15][N:14]([C:18]([N:20]3[CH2:23][CH:22]([O:24][C:25]4[CH:26]=[CH:27][C:28]([C:31]([CH3:37])([CH3:36])[C:32](OC)=[O:33])=[N:29][CH:30]=4)[CH2:21]3)=[O:19])[CH2:13][CH2:12]2)[CH2:10][CH2:9][CH2:8]1>C1COCC1>[CH:7]1([N:11]2[CH2:17][CH2:16][CH2:15][N:14]([C:18]([N:20]3[CH2:21][CH:22]([O:24][C:25]4[CH:26]=[CH:27][C:28]([C:31]([CH3:37])([CH3:36])[CH2:32][OH:33])=[N:29][CH:30]=4)[CH2:23]3)=[O:19])[CH2:13][CH2:12]2)[CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58243401HCID 58243401, compound

Product 1

HCID 58243390HCID 58243390, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 0° C. solution of LiAlH4 (0.56 ml, 0.562 mmol, 1M in THF) in THF (1 ml) under a nitrogen atmosphere was added methyl 2-[5-({1-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidin-3-yl}oxy)pyridin-2-yl]-2-methylpropanoate (110 mg, 62% UV purity) in THF (1 ml). TLC analysis of the reaction mixture after 30 minutes indicated complete consumption of starting material. Water (1 ml), 2M NaOH (1 ml), and water (1 ml) were cautiously added to the reaction mixture. The mixture was diluted with EtOAc (20 ml), dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by FCC on silica gel [eluting with 5% methanolic ammonia (7N) in DCM] to provide the title compound as colourless oil (34.5 mg).

Workup

  1. customconsumption of starting material
  2. additionWater (1 ml), 2M NaOH (1 ml), and water (1 ml) were cautiously added to the reaction mixture
  3. additionThe mixture was diluted with EtOAc (20 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by FCC on silica gel [eluting with 5% methanolic ammonia (7N) in DCM]

Sources & evidence

ORD record
ord-c890eeb0568e4f6f9c5940425ab8010d
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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