Hydrochloric Acid → Methyl 1-amino-1-cyclopentanecarboxylate, HCl

HRID 1615789Notes

Reaction equation

HRID 1615789 reaction equation
[NH2:1][C:2]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.[ClH:10].[CH3:11]O>>[ClH:10].[NH2:1][C:2]1([C:7]([O:9][CH3:11])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 2901Cycloleucine

Product 1

HCID 11513856Methyl 1-amino-1-cyclopentanecarboxylate, HCl

Procedure

A solution of 1-aminocyclopentanecarboxylic acid (20.0 g, 155 mmol) in MeOH (300 mL) was saturated with HCl (g), aged for 30 min, and saturated again with HCl (g). The mixture was aged at ambient temperature for 2 h and concentrated to dryness in vacuo. To the white solid was added saturated aqueous NaHCO3 (350 mL), carefully, with ice cooling, and the resulting mixture was extracted with EtOAc (4×250 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS: m/z=144 (M+1).

Workup

  1. waitThe mixture was aged at ambient temperature for 2 h
  2. concentrationconcentrated to dryness in vacuo
  3. additionTo the white solid was added saturated aqueous NaHCO3 (350 mL)
  4. extractioncarefully, with ice cooling, and the resulting mixture was extracted with EtOAc (4×250 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-071462f5a7244e2eb4ec0f296f63b261
Source dataset
uspto-grants-2014_07
Patent number
US08765759B2

Reaction notes

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