Aluminium lithium hydride → HCID 178453600, compound

HRID 1984866Notes

Reaction equation

HRID 1984866 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12](=[O:25])[NH:13][CH2:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([CH2:21][N:22]=[N+]=[N-])[CH2:17][CH2:16]1)([CH3:10])([CH3:9])[CH3:8]>C1COCC1>[C:7]([O:11][C:12](=[O:25])[NH:13][CH2:14][C@H:15]1[CH2:16][CH2:17][C@H:18]([CH2:21][NH2:22])[CH2:19][CH2:20]1)([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178453603HCID 178453603, compound

Product 1

HCID 178453600HCID 178453600, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of lithium aluminum hydride (2.76 g, 72.6 mmol) in THF (225 mL) was cooled at 0° C. and a solution of trans-(4-azidomethyl-cyclohexylmethyl)-carbamic acid tert-butyl ester (15.0 g, 55.9 mmol) in THF (75 mL) was added over 1 hr. The reaction mixture was stirred at ambient temperature for 6 hr. The reaction was quenched with Na2SO4.10H2O, filtered through a pad of celite, and concentrated. The residue was purified by flash chromatography (silica gel, 50% MeOH in CHCl3) to give trans-(4-aminomethyl-cyclohexylmethyl)-carbamic acid tert-butyl ester (12.3 g, 91%) as a pale yellow oil.

Workup

  1. customThe reaction was quenched with Na2SO4.10H2O
  2. filtrationfiltered through a pad of celite
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography (silica gel, 50% MeOH in CHCl3)

Sources & evidence

ORD record
ord-0a614d54f64a4322bc3d88e84fda0137
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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