Aluminium lithium hydride → HCID 68887617, compound

HRID 1432345Notes

Reaction equation

HRID 1432345 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([O:11][C:12](=[O:27])[NH:13][C@@H:14]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C@H:15]([OH:19])[CH2:16][C:17]#[N:18])([CH3:10])([CH3:9])[CH3:8]>C1COCC1>[C:7]([O:11][C:12](=[O:27])[NH:13][C@@H:14]([CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C@H:15]([OH:19])[CH2:16][CH2:17][NH2:18])([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68888451HCID 68888451, compound

Product 1

HCID 68887617HCID 68887617, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of LAH (0.6 g) in THF (40 ml) is added at 0° C. a solution of ((1S,2R)-1-Benzyl-3-cyano-2-hydroxy-propyl)-carbamic acid tert-butyl ester (1.1 g) in THF (15 ml). The mixture is stirred for 1 h at 0° C. and then quenched with water and 3N aqueous sodium hydroxide. After filtration the solution is concentrated under reduced pressure and purified by preparative HPLC (gradient of water, 0.1% TFA/acetonitrile, 0.1% TFA from 80/20 to 0/100 on Nucleosil 100-10 C18 column). The fractions containing ((1S,2R)-4-Amino-1-benzyl-2-hydroxy-butyl)-carbamic acid tert-butyl ester are set to a basic pH by addition of soda and extracted with EtOAc. The organic layer is dried over sodium sulfate and concentrated under reduced pressure to give 682 mg of the desired product.

Workup

  1. customquenched with water and 3N aqueous sodium hydroxide
  2. filtrationAfter filtration the solution
  3. concentrationis concentrated under reduced pressure
  4. custompurified by preparative HPLC (gradient of water, 0.1% TFA/acetonitrile, 0.1% TFA from 80/20 to 0/100 on Nucleosil 100-10 C18 column)
  5. additionThe fractions containing ((1S,2R)-4-Amino-1-benzyl-2-hydroxy-butyl)-carbamic acid tert-butyl ester
  6. additionare set to a basic pH by addition of soda
  7. extractionextracted with EtOAc
  8. dry with materialThe organic layer is dried over sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8027bad18e764a1398c0a05adc78b7e5
Source dataset
uspto-grants-2009_11
Patent number
US07612054B2

Reaction notes

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