Aluminium lithium hydride → HCID 90119687, compound

HRID 2202547Notes

Reaction equation

HRID 2202547 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:25](N(OC)C)=[O:26])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH:25]=[O:26])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90120002HCID 90120002, compound

Product 1

HCID 90119687HCID 90119687, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a stirred solution of D1 in THF (0.15 M) cooled to −20° C., was added dropwise a 1.0 M solution of LiAlH4 in THF (1.25 eq.). Reaction mixture was stirred at −20° C. for 30 min before quenching with EtOAc and partitioning between EtOAc and 0.1 M HCl. The organic phase was separated and the aqueous phase extracted into EtOAc. The combined organic extracts were washed with H2O, brine, dried over Na2SO4 and concentrated under reduced pressure to give the title compound as pale yellow oil which was used in the next step without further purification. MS (ES+) C20H29NO5: 364 (M+H)+.

Workup

  1. customReaction mixture
  2. custombefore quenching with EtOAc
  3. custompartitioning between EtOAc and 0.1 M HCl
  4. customThe organic phase was separated
  5. extractionthe aqueous phase extracted into EtOAc
  6. washThe combined organic extracts were washed with H2O, brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6b8dfea0733d41db809b4574c082a66f
Source dataset
uspto-grants-2016_06
Patent number
US09365541B2

Reaction notes

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