(S)-Benzyl 3-((1-(tert-butoxycarbonyl)azetidin-3-yl)amino)pyrrolidine-1-carboxylate → (S)-tert-Butyl-3-(pyrrolidin-3-ylamino)azetidine-1-carboxylate

HRID 403285Notes

Reaction equation

HRID 403285 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([NH:12][C@H:13]2[CH2:17][CH2:16][N:15](C(OCC3C=CC=CC=3)=O)[CH2:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CCO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([NH:12][C@H:13]2[CH2:17][CH2:16][NH:15][CH2:14]2)[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 67475267(S)-Benzyl 3-((1-(tert-butoxycarbonyl)azetidin-3-yl)amino)pyrrolidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 67289806(S)-tert-Butyl-3-(pyrrolidin-3-ylamino)azetidine-1-carboxylateYield 98.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of compound 5b (1.3 g, 3.46 mmol), 10% Pd/C (200 mg) in EtOH (50 mL) was hydrogenated under 40 psi hydrogen pressure in a Parr apparatus for 4.5 h. The reaction was filtered through a pad of diatomaceous earth and the organic solution was concentrated and dried under vacuum to give compound 5c as a thick oil (0.825 g). 1H NMR (300 MHz, CDCl3): δ 4.10 (m, 2H), 3.64-3.55 (m, 3H), 3.23 (m, 1H), 3.05 (m, 1H), 2.97-2.85 (m, 2H), 2.68 (m, 1H), 1.97 (m, 1H), 1.51 (m, 1H), 1.43 (s, 9H).

Workup

  1. filtrationThe reaction was filtered through a pad of diatomaceous earth
  2. concentrationthe organic solution was concentrated
  3. customdried under vacuum

Sources & evidence

ORD record
ord-5beaca52af1449cc886024f2ac93559b
Source dataset
uspto-grants-2014_06
Patent number
US08748417B2

Reaction notes

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