(2S-trans)-4-cyclohexyl-5-oxo-2-pyrrolidinemethanol → (2S-trans)-4-cyclohexyl-2-pyrrolidinemethanol

HRID 1732125Notes

Reaction equation

HRID 1732125 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([C@H:13]2[C:17](=O)[NH:16][C@H:15]([CH2:19][OH:20])[CH2:14]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>O1CCCC1>[CH:7]1([C@H:13]2[CH2:17][NH:16][C@H:15]([CH2:19][OH:20])[CH2:14]2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 13648265(2S-trans)-4-cyclohexyl-5-oxo-2-pyrrolidinemethanolHCID 21226445Aluminium lithium hydride

Product 1

HCID 13648259(2S-trans)-4-cyclohexyl-2-pyrrolidinemethanolYield 37.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of lithium aluminum hydride (0.8 g) in 50 ml of tetrahydrofuran was added (2S-trans)-4-cyclohexyl-5-oxo-2-pyrrolidinemethanol (2.0 g) in 20 ml of tetrahydrofuran. After the addition, the mixture was refluxed for 24 hours, cooled to 0° C., quenched with ethyl acetate followed by saturated sodium sulphate solution, filtered, and the filtrate dried over anhydrous magnesium sulphate. Removal of the solvent followed by crystallization yielded 0.7 g of (2S-trans)-4-cyclohexyl-2-pyrrolidinemethanol as white crystals, melting point 98°-99° C.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed for 24 hours
  3. customquenched with ethyl acetate
  4. filtrationfiltered
  5. dry with materialthe filtrate dried over anhydrous magnesium sulphate
  6. customRemoval of the solvent
  7. customfollowed by crystallization

Sources & evidence

ORD record
ord-869882e769cd4b929c23c4be5733cb00
Source dataset
uspto-grants-1986_11
Patent number
US04625038

Reaction notes

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