Ammonium formate → HCID 58365097, compound

HRID 60309Notes

Reaction equation

HRID 60309 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:24][CH2:25][CH2:26][F:27])[C@H:9]1[CH2:13][CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+].[H][H]>CO.[Pd]>[F:27][CH2:26][CH2:25][CH2:24][N:8]([C@H:9]1[CH2:13][CH2:12][NH:11][CH2:10]1)[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 2723923Ammonium formateHCID 58365182(S)-benzyl 3-(tert-butoxycarbonyl(3-fluoropropyl)amino)pyrrolidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 58365097HCID 58365097, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-benzyl 3-(tert-butoxycarbonyl(3-fluoropropyl)amino)pyrrolidine-1-carboxylate (611 mg, 1.6 mmol) in methanol (6.5 mL) was added ammonium formate (1.1 g, 18 mmol) followed palladium on carbon (10% w/w, 479 mg, 0.22 mmol). The reaction mixture was stirred at ambient temperature under a balloon of hydrogen for 1 hour, then degassed and filtered over a pad of celite. The filtrate was concentrated in vacuo to afford a residue, which was used in the next step without any further purification.

Workup

  1. customdegassed
  2. filtrationfiltered over a pad of celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto afford a residue, which
  5. customwas used in the next step without any further purification

Sources & evidence

ORD record
ord-60212bc2e21c4f38bafe7eef674ffb53
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

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