Aluminium lithium hydride → HCID 59683370, compound

HRID 2221293Notes

Reaction equation

HRID 2221293 reaction equation
C(O[C:6](=O)[NH:7][CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([C:19](=O)[N:20]([CH3:22])[CH3:21])=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:22][N:20]([CH2:19][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[C:9]([CH2:8][NH:7][CH3:6])=[CH:10][CH:11]=[CH:12]2)[CH3:21]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59683375HCID 59683375, compound

Product 1

HCID 59683370HCID 59683370, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a room temperature solution of (6-dimethylcarbamoyl-naphthalen-1-ylmethyl)-carbamic acid tert-butyl ester, 8, (20.45 g, 62.4 mmol) in anhydrous THF (300 mL) is added 1 M LAH in THF (125 mL, 2 eq.). After the addition is complete the resulting solution is heated at reflux for 3 hours. The reaction solution is then cooled in an ice bath and quenched by the addition of water (2.7 mL). The resulting mixture is dried over MgSO4. The solid is removed by filtration and the filtrate concentrated in vacuo to afford 14.25 g of the desired product as a colorless oil. LRMS: 229.05 (M+1).

Workup

  1. additionAfter the addition
  2. temperatureis heated
  3. temperatureat reflux for 3 hours
  4. temperatureThe reaction solution is then cooled in an ice bath
  5. customquenched by the addition of water (2.7 mL)
  6. dry with materialThe resulting mixture is dried over MgSO4
  7. customThe solid is removed by filtration
  8. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-6059448e65a749bf8c33d194b7fcd9fe
Source dataset
uspto-grants-2008_05
Patent number
US07368462B1

Reaction notes

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