Aluminium lithium hydride → HCID 86730157, compound

HRID 1850125Notes

Reaction equation

HRID 1850125 reaction equation
Cl.[NH2:2][C@H:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9](OC)=[O:10])=[CH:7][C:6]=1[F:15])[CH3:4].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:2][C@H:3]([C:5]1[CH:14]=[CH:13][C:8]([CH2:9][OH:10])=[CH:7][C:6]=1[F:15])[CH3:4]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86730158HCID 86730158, compound

Product 1

HCID 86730157HCID 86730157, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) suspension of (S)-methyl 4-(1-aminoethyl)-3-fluorobenzoate hydrochloride (0.109 g, 0.468 mmol) in THF (15 mL) was added a solution of LAH in THF (2.0 M, 1.05 mL, 2.10 mmol, 4.49 equiv) and the resulting mixture was stirred at 0° C. for 2 h 20 min and at room temperature for 2½ h. The reaction mixture was quenched by addition of a mixture of Na2SO4 decahydrate and Celite (1:1 by weight) until gas evolution ceased. The reaction mixture was filtered, washed with EtOAc. The filtrate was concentrated and used for the next reaction without purification.

Workup

  1. temperatureTo a cooled
  2. customThe reaction mixture was quenched by addition of a mixture of Na2SO4 decahydrate and Celite (1:1 by weight) until gas evolution
  3. filtrationThe reaction mixture was filtered
  4. washwashed with EtOAc
  5. concentrationThe filtrate was concentrated
  6. customused for the next reaction without purification

Sources & evidence

ORD record
ord-4999a0cbb1bd404c99ea5ee4bdd34bd4
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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