Water → 3-Hydroxy-4-aminomethyl-1-phenylmethyl pyrrolidine

HRID 1031576Notes

Reaction equation

HRID 1031576 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][CH:8]1[CH:12]([C:13]([NH2:15])=O)[CH2:11][N:10]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9]1.ClCCl.O>O1CCCC1>[OH:7][CH:8]1[CH:12]([CH2:13][NH2:15])[CH2:11][N:10]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 148395853-Hydroxy-4-aminocarbonyl-1-phenylmethyl pyrrolidineHCID 21226445Aluminium lithium hydride

Product 1

HCID 139598933-Hydroxy-4-aminomethyl-1-phenylmethyl pyrrolidineYield 90.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a dry flask was place 1.34 g (35.0 mmol) of lithium aluminum hydride in 20 ml dry tetrahydrofuran cooled to -5° C. To this suspension was added dropwise 2.58 g (11.7 mmol) of 3-hydroxy-4-aminocarbonyl-1-phenylmethyl pyrrolidine. After completion of addition the suspension was warmed 2 hours under reflux, cooled. It was successively added 35 ml dichloromethane, 50 ml tetrahydrofuran and 2.3 ml water. The suspension was passed through a celite pad. The solvent removed to give 2.19 g (90.8%) of title compound as an oil.

Workup

  1. customIn a dry flask was
  2. additionAfter completion of addition the suspension
  3. temperaturewas warmed 2 hours
  4. temperatureunder reflux
  5. temperaturecooled
  6. customThe solvent removed

Sources & evidence

ORD record
ord-f209ef89371449dcbcad5041110b0731
Source dataset
uspto-grants-1990_09
Patent number
US04954507

Reaction notes

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