Aluminium lithium hydride → Tert-butyl 3-amino-1-(4-chlorophenyl)propylcarbamate

HRID 423045Notes

Reaction equation

HRID 423045 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:15][C:16]#[N:17])=[CH:10][CH:9]=1>C1COCC1>[NH2:17][CH2:16][CH2:15][CH:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])[C:11]1[CH:10]=[CH:9][C:8]([Cl:7])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57750327Tert-butyl 1-(4-chlorophenyl)-2-cyanoethylcarbamate2×

Product 1

HCID 24729697Tert-butyl 3-amino-1-(4-chlorophenyl)propylcarbamateYield 100.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

Lithium aluminium hydride (0.712 mL, 0.71 mmol) was added dropwise to tert-butyl 1-(4-chlorophenyl)-2-cyanoethylcarbamate (Intermediate 24) (200 mg, 0.71 mmol) in THF (4 mL) at 20° C. under nitrogen. The resulting solution was stirred at 20° C. for 2 hours. The reaction mixture was quenched with NaOH (1M) (1 mL) and the solution was filtered. The solution was diluted with EtOAc (20 mL), and washed with water 2× (10 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford tert-butyl 3-amino-1-(4-chlorophenyl)propylcarbamate (203 mg, 100%) as a gum. m/z (ESI+) (M+H)+=285; HPLC tR=2.33 min.

Workup

  1. customThe reaction mixture was quenched with NaOH (1M) (1 mL)
  2. filtrationthe solution was filtered
  3. additionThe solution was diluted with EtOAc (20 mL)
  4. washwashed with water 2× (10 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-ed4e5e0bfb5a48f58552c759f91e22ab
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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