(2S)-1-Triphenylmethyl-2-pyrrolidinecarboxylic acid methyl ester → HCID 21575548, compound

HRID 743720Notes

Reaction equation

HRID 743720 reaction equation
[C:1]([N:20]1[CH2:24][CH2:23][CH2:22][CH:21]1[C:25](OC)=[O:26])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[C:1]([N:20]1[CH2:24][CH2:23][CH2:22][CH:21]1[CH2:25][OH:26])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 273737(2S)-1-Triphenylmethyl-2-pyrrolidinecarboxylic acid methyl esterHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 21575548HCID 21575548, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
22 °C

Procedure

A solution of 5.00 g (13.4 mmol) of the above ester in 50 mL of diethyl ether is added dropwise to a mixture of 0.509 g (13.4 mmol) of solid lithium aluminum hydride in 10 mL of ether while stirring under nitrogen. The mixture is brought to a gentle reflux and an additional 6.7 mL (6.7 mmol) of a 1M solution of lithium aluminum hydride in ether is injected by syringe. After refluxing for 2 hrs the reaction is cooled to 22° C. and quenched with 10 mL of methanol. The mixture is partitioned between 100 mL of 0.5M NaOH and 50 mL of ether and then stirred vigorously for 25 minutes and filtered. The ether layer is separated, washed with brine (30 mL), dried (MgSO4) and evaporated to give 4.20 g of (1-tritylpyrrolidin-2-yl)methanol as a white foam. By the method described in preparation 2, this material is used to prepare the title compound which is recrystallized from ethyl acetate/hexane.

Workup

  1. temperaturea gentle reflux
  2. temperatureAfter refluxing for 2 hrs the reaction
  3. customquenched with 10 mL of methanol
  4. customThe mixture is partitioned between 100 mL of 0.5M NaOH and 50 mL of ether
  5. stirringstirred vigorously for 25 minutes
  6. filtrationfiltered
  7. customThe ether layer is separated
  8. washwashed with brine (30 mL)
  9. dry with materialdried (MgSO4)
  10. customevaporated

Sources & evidence

ORD record
ord-8c83582321304107936700db15df78df
Source dataset
uspto-grants-1996_09
Patent number
US05556990

Reaction notes

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