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

HRID 2108805Notes

Reaction equation

HRID 2108805 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-13aea4dfc2dc47cea3bf581fa7518ca5
Source dataset
uspto-grants-2009_04
Patent number
US07514451B2

Reaction notes

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