Aluminium lithium hydride → HCID 68616639, compound

HRID 1158480Notes

Reaction equation

HRID 1158480 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]([NH:10][C:11]([C@H:13]1[C@@H:17]([CH2:18][OH:19])[CH2:16][N:15]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:14]1)=O)([CH3:9])[CH3:8]>C1COCC1>[CH2:20]([N:15]1[CH2:14][C@@H:13]([CH2:11][NH:10][CH:7]([CH3:8])[CH3:9])[C@@H:17]([CH2:18][OH:19])[CH2:16]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68616172HCID 68616172, compound

Product 1

HCID 68616639HCID 68616639, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a ice-cooled solution of LiAlH4 (0.56 g, 14.76 mmol) in THF (25 mL), is added dropwise a solution of (3S*,4R*)-1-benzyl-4-hydroxymethyl-pyrrolidine-3-carboxylic acid isopropylamide (1.02 g, 3.69 mmol) in THF (5 mL). The reaction mixture is refluxed overnight and quenched with Na2SO4.10H2O (4 g) at 0° C. Ether is added, the mixture is stirred for 2 h at room temperature. The crude material is filtered over a pad of Celite and concentrated to give the title compound which is used without further purification in the next step. TLC, Rf (CH2Cl2/MeOH 95:5)=0.28. MS (LC-MS): 263.2 [M+H]+; ]+; tR (HPLC, C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/2.5 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 2.94 min.

Workup

  1. temperatureThe reaction mixture is refluxed overnight
  2. customquenched with Na2SO4.10H2O (4 g) at 0° C
  3. additionEther is added
  4. filtrationThe crude material is filtered over a pad of Celite
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-55b4d1c343634d9db0070c556980d50f
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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