Hydrochloric Acid → (2S,3S)-2-Amino-3-methyl-1-(3,3,4,4-tetrafluoro-pyrrolidin-1-yl)-pentan-1-one Hydrochloride

HRID 49761Notes

Reaction equation

HRID 49761 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:13]([N:15]1[CH2:19][C:18]([F:21])([F:20])[C:17]([F:23])([F:22])[CH2:16]1)=[O:14])[C@@H:9]([CH3:12])[CH2:10][CH3:11])(C)(C)C.[ClH:25]>C(OCC)(=O)C>[ClH:25].[NH2:7][C@@H:8]([C@@H:9]([CH3:12])[CH2:10][CH3:11])[C:13]([N:15]1[CH2:19][C:18]([F:20])([F:21])[C:17]([F:23])([F:22])[CH2:16]1)=[O:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86590627[(1S,2S)-2-Methyl-1-(3,3,4,4-tetrafluoro-pyrrolidine-1-carbonyl)-butyl]-carbamic acid tert-butyl ester

Product 1

HCID 9882539(2S,3S)-2-Amino-3-methyl-1-(3,3,4,4-tetrafluoro-pyrrolidin-1-yl)-pentan-1-one Hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

[(1S, 2S)-2-Methyl-1-(3,3,4,4-tetrafluoro-pyrrolidine-1-carbonyl)-butyl]-carbamic acid tert-butyl ester (200 mg, 0.56 mmol) was dissolved in ethyl acetate (4 mL), cooled to ° C. and treated with gaseous HCl for about 1 minute. After 15 minute at 0° C. and 30 minute at room temperature, the mixture was concentrated to dryness and the solid was triturated with hexane, collected and dried under vacuum overnight (124 mg, 76%, mp>250° C.).

Workup

  1. temperaturecooled
  2. concentration30 minute at room temperature, the mixture was concentrated to dryness
  3. customthe solid was triturated with hexane
  4. customcollected
  5. customdried under vacuum overnight (124 mg, 76%, mp>250° C.)

Sources & evidence

ORD record
ord-35af9e7bd94b4eb2b10dd944f6c0cc4a
Source dataset
uspto-grants-2004_03
Patent number
US06710040B1

Reaction notes

Loading…