Aluminium lithium hydride → HCID 67126802, compound

HRID 1520696Notes

Reaction equation

HRID 1520696 reaction equation
[F:1][C:2]1([C:12](OCC)=[O:13])[CH2:7][CH2:6][N:5]([CH:8]2[CH2:11][O:10][CH2:9]2)[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:1][C:2]1([CH2:12][OH:13])[CH2:3][CH2:4][N:5]([CH:8]2[CH2:9][O:10][CH2:11]2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67126714HCID 67126714, compound

Product 1

HCID 67126802HCID 67126802, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 517A (0.59 g) in tetrahydrofuran (5 mL) was added lithium aluminum hydride (1.8 mL) at 0° C. The reaction was removed from the ice bath and allowed to warm to room temperature. The reaction was quenched by the dropwise addition of 0.6 mL of water followed by 0.2 ml of 2N aqueous NaOH. The reaction was filtered through diatomaceous earth, rinsed with ethyl acetate (50 mL) and concentrated. Silica gel chromatography over silica gel (Reveleris 40 g) eluting with a gradient of 0.75% to 7.5% methanol/dichloromethane over 30 minutes (flow=40 ml/minutes) gave the title compound.

Workup

  1. customThe reaction was removed from the ice bath
  2. customThe reaction was quenched by the dropwise addition of 0.6 mL of water
  3. filtrationThe reaction was filtered through diatomaceous earth
  4. washrinsed with ethyl acetate (50 mL)
  5. concentrationconcentrated
  6. washSilica gel chromatography over silica gel (Reveleris 40 g) eluting with a gradient of 0.75% to 7.5% methanol/dichloromethane over 30 minutes (flow=40 ml/minutes)

Sources & evidence

ORD record
ord-46392d7e2c314e2284bde682cb607c15
Source dataset
uspto-grants-2015_07
Patent number
US09073855B2

Reaction notes

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