Aluminium lithium hydride → HCID 69870158, compound

HRID 1359855Notes

Reaction equation

HRID 1359855 reaction equation
OC(C(F)(F)F)=O.[CH:8]1([NH:11][C:12]([C@@H:14]2[CH2:18][C@@H:17]([OH:19])[CH2:16][NH:15]2)=O)[CH2:10][CH2:9]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.O.[OH-].[Na+]>[CH:8]1([NH:11][CH2:12][C@H:14]2[NH:15][CH2:16][C@H:17]([OH:19])[CH2:18]2)[CH2:9][CH2:10]1

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 131724000HCID 131724000, compound

Product 1

HCID 69870158HCID 69870158, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (2S,4R)-4-hydroxy-pyrrolidine-2-carboxylic acid cyclopropylamide TFA salt (from the above reaction) and LAH (910 mg, excess) in THF was heated to reflux for 4 hours. The reaction was cooled to 0° C., diluted with water (0.9 mL), 10% NaOH (0.9 mL) and then water (0.9 mL). The mixture was stirred for 30 mins, the insolubles were filtered off, the filtrate was concentrated and dried to give 900 mg of (3R, 5S)-5-cyclopropylaminomethyl-pyrrolidin-3-ol as a colorless oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. filtrationthe insolubles were filtered off
  4. concentrationthe filtrate was concentrated
  5. customdried

Sources & evidence

ORD record
ord-a630b8a335d64aa886fada77d6cab950
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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