Ammonium formate → HCID 131718420, compound

HRID 1034502Notes

Reaction equation

HRID 1034502 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][O:8][C:9]([N:11]2[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:12]2[CH2:17][N:18]=[N+]=[N-])=[O:10])=[CH:5][CH:4]=1.C([O-])=O.[NH4+]>CO.[Pd].ClCCl>[CH:9]([OH:10])=[O:8].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]([N:11]2[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:12]2[CH2:17][NH2:18])=[O:10])=[CH:21][CH:22]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 57029350HCID 57029350, compound

Product 1

HCID 131718420HCID 131718420, compoundYield 144.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of the thus obtained (2S,4R)-1-p-methoxybenzyloxycarbonyl-4-hydroxy-2-azidomethylpyrrolidine (5.57 g: 18.18 mmole) in methanol (30 ml) are added, 5% palladium on charcoal (560 mg) and ammonium formate (2.3 g). The mixture is stirred at 45° C. for 2 hours. The reaction mixture is diluted with dichloromethane (50 ml), filtered to remove the catalyst, and concentrated in vacuo. The residue is crystallized from a mixture of dichloromethane and ether and washed with ether to give (2S,4R)-1-p-methoxybenzyloxycarbonyl-4-hydroxy-2-aminomethylpyrrolidine formate (4.28 g). Yield: 72%. NMR δ(CDCl3 --CD3OD) ppm: 1.6 to 1.82(m, 1H), 2.1 to 2.3(m, 1H), 2.7 to 3.7(m, 4H), 3.81(s, 3H), 4.1 to 4.4(m, 2H), 5.04(s, 2H), 6.88(d, J=8.8 Hz, 2H), 7.28(d, J=8.8 Hz, 2H), 8.47(s, 1H). IR ν (CHCl3) cm-1 : 3678, 3412, 1678, 1602.

Workup

  1. filtrationfiltered
  2. customto remove the catalyst
  3. concentrationconcentrated in vacuo
  4. customThe residue is crystallized from a mixture of dichloromethane and ether
  5. washwashed with ether

Sources & evidence

ORD record
ord-87a5411ccc82435f9f6d893fd31e0629
Source dataset
uspto-grants-1994_05
Patent number
US05317016

Reaction notes

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