(3S,4S)-1-benzyloxycarbonyl-3-cyclopropylaminomethyl-4-fluoropyrrolidine → N-(((3R,4S)-4-Fluoropyrrolidin-3-yl)methyl)cyclopropanamine

HRID 424742Notes

Reaction equation

HRID 424742 reaction equation
C(OC([N:11]1[CH2:15][C@@H:14]([F:16])[C@@H:13]([CH2:17][NH:18][CH:19]2[CH2:21][CH2:20]2)[CH2:12]1)=O)C1C=CC=CC=1.[H][H]>C(O)C.[C].[Pd]>[CH:19]1([NH:18][CH2:17][C@@H:13]2[C@H:14]([F:16])[CH2:15][NH:11][CH2:12]2)[CH2:21][CH2:20]1

Participants

5

Reactant 2

HCID 53307702(3S,4S)-1-benzyloxycarbonyl-3-cyclopropylaminomethyl-4-fluoropyrrolidineHCID 178418361HCID 178418361, compound

Product 1

HCID 11147857N-(((3R,4S)-4-Fluoropyrrolidin-3-yl)methyl)cyclopropanamineYield 92%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

(3S,4S)-1-Benzyloxycarbonyl-3-cyclopropylaminomethyl-4-fluoropyrrolidine (2.29 g) was dissolved in ethanol (25 mL). To this solution, 10% palladium carbon (229 mg) was added and the mixture was stirred at room temperature for 1.5 hours under a stream of hydrogen gas. The catalyst in the reaction mixture was filtered and was washed with ethanol. The filtrate and the washings were combined and concentrated under reduced pressure. The resulting residue was distilled under reduced pressure to give (3R,4S)-3-cyclopropylaminomethyl-4-fluoropyrrolidine as a colorless oil (1.14 g). This compound was identical to the compound obtained in Reference Example 8 (Process I).

Workup

  1. filtrationThe catalyst in the reaction mixture was filtered
  2. washwas washed with ethanol
  3. concentrationconcentrated under reduced pressure
  4. distillationThe resulting residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-16daad5e5e5440c48c0633c5c0400016
Source dataset
uspto-grants-2012_01
Patent number
US08106072B2

Reaction notes

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