Aluminium lithium hydride → HCID 18545202, compound

HRID 1266989Notes

Reaction equation

HRID 1266989 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([CH:12]1[CH2:16][CH2:15][CH:14]([C:17](OCC)=[O:18])[N:13]1[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)=O)C.ClC1C=CC(N2[C@@H](CO)CC[C@@H]2CO)=CC=1>O1CCCC1>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([N:13]2[CH:12]([CH2:10][OH:9])[CH2:16][CH2:15][CH:14]2[CH2:17][OH:18])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 57440110HCID 57440110, compoundHCID 86585102HCID 86585102, compound

Product 1

HCID 18545202HCID 18545202, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (1.0 M in tetrahydrofuran, 20.7 mL) was added to tetrahydrofuran (68 mL) at 0° C. 1-(4-Chloro-phenyl)-pyrrolidine-2,5-dicarboxylic acid diethyl ester (4.50 g, 13.81 mmol) in tetrahydrofuran (17 mL) was added rapidly dropwise and the mixture was stirred at room temperature for 4 hours. Mix was quenched by careful addition of water (2.5 mL) followed by 10% sodium hydroxide (1.7 mL) and stirred for 15 h then filtered through Celite and the cake was washed with ethyl acetate (2×100 mL). The filtrate was dried with magnesium sulfate and concentrated to yield a mixture of cis and trans [1-(4-Chloro-phenyl)-5-hydroxymethyl-pyrrolidin-2-yl]-methanol (3.34 g, 100%) as a golden oil. Oil was used without further purification.

Workup

  1. additionMix
  2. customwas quenched by careful addition of water (2.5 mL)
  3. stirringstirred for 15 h
  4. filtrationthen filtered through Celite
  5. washthe cake was washed with ethyl acetate (2×100 mL)
  6. dry with materialThe filtrate was dried with magnesium sulfate
  7. concentrationconcentrated
  8. customto yield
  9. customOil was used without further purification

Sources & evidence

ORD record
ord-9c524b1ac3cf418c88397d0b9de44c0d
Source dataset
uspto-grants-2003_04
Patent number
US06552015B2

Reaction notes

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