Aluminium lithium hydride → HCID 117729562, compound

HRID 711167Notes

Reaction equation

HRID 711167 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([NH2:15])=[CH:13][C:12]([C:16]([CH3:19])([CH3:18])[CH3:17])=[N:11]2)=[CH:6][C:5]=1[O:20][CH2:21][CH2:22][O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:15][C:14]1[N:10]([C:7]2[CH:8]=[CH:9][C:4]([CH2:3][OH:2])=[C:5]([O:20][CH2:21][CH2:22][O:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)[CH:6]=2)[N:11]=[C:12]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 117729773HCID 117729773, compound

Product 1

HCID 117729562HCID 117729562, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Intermediate 55b (1.72 g, 4.12 mmol) in THF (30 mL) was treated with LiAlH4 (2M in THF, 2.5 mL, 4.94 mmol) [CARE: gas evolution]. The reaction mixture was left to stir at RT for 5 h. The reaction was quenched slowly with water and the product was extracted with EtOAc. The organic phase was separated, washed with brine, dried over Na2SO4, and evaporated under reduced pressure to give the title compound (1.57 g, 95%). LCMS (Method 3): Rt 2.80 min, m/z 390 [MH+].

Workup

  1. waitThe reaction mixture was left
  2. customThe reaction was quenched slowly with water
  3. extractionthe product was extracted with EtOAc
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8e1149c80b1442f1997c37d47a0f443d
Source dataset
uspto-grants-2015_11
Patent number
US09181242B2

Reaction notes

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