Hydrochloric Acid → Tetrahydro-1H-pyrrolizine-7a(5H)-carboxylic acid hydrochloride

HRID 569733Notes

Reaction equation

HRID 569733 reaction equation
C([O:3][C:4]([C:6]12[CH2:13][CH2:12][CH2:11][N:10]1[CH2:9][CH2:8][CH2:7]2)=[O:5])C.[ClH:14]>[OH-].[Na+].C(O)C>[ClH:14].[CH2:13]1[C:6]2([C:4]([OH:5])=[O:3])[N:10]([CH2:9][CH2:8][CH2:7]2)[CH2:11][CH2:12]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 107975451H-Pyrrolizine-7a(5H)-carboxylic acid, tetrahydro-, ethyl ester

Product 1

HCID 44118652Tetrahydro-1H-pyrrolizine-7a(5H)-carboxylic acid hydrochlorideYield 92.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of pyrrolizidine-7a-carboxylic acid ethylester (35.4 g, 0.193 mol) in 360 ml of 10% aqueous sodium hydroxide solution and 360 ml of ethanol was stirred at 10° to 15° C. for 2.5 hours. The reaction mixture was acidified with concentrated hydrochloric acid and then evaporated in vacuo to dryness. After addition of ethanol to the remaining residue, undissolved sodium chloride was filtered-off and the filtrate was evaporated in vacuo to dryness. The purifying operation described above was repeated twice. To the remaining residue, acetone was added to form crystals. The crystals were obtained through filtration and washed with small amount of acetone to give 34.2 g (92.4%) of the desired compound.

Workup

  1. customevaporated in vacuo to dryness
  2. additionAfter addition of ethanol to the remaining residue, undissolved sodium chloride
  3. customthe filtrate was evaporated in vacuo to dryness
  4. additionTo the remaining residue, acetone was added
  5. customto form crystals
  6. customThe crystals were obtained through filtration
  7. washwashed with small amount of acetone

Sources & evidence

ORD record
ord-3ed261a95fc34363be75f290ed83a36f
Source dataset
uspto-grants-1988_03
Patent number
US04734411

Reaction notes

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