Aluminium lithium hydride → HCID 67126802, compound

HRID 2040318Notes

Reaction equation

HRID 2040318 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 372A (0.59 g) in tetrahydrofuran (5 mL) was added lithium aluminum hydride (1.80 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 and rinsed with ethyl acetate (50 mL). The organics were concentrated and loaded onto silica gel (Reveleris 40 g) and eluted using a gradient of 0.75% to 7.5% methanol/dichloromethane over 30 minute (flow=40 mL/minutes) to give 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. concentrationThe organics were concentrated and loaded onto silica gel (Reveleris 40 g)
  6. washeluted
  7. customover 30 minute

Sources & evidence

ORD record
ord-97a6255130e94ae8b2e82fad441fed9f
Source dataset
uspto-grants-2013_11
Patent number
US08580794B2

Reaction notes

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