Ammonium formate → HCID 68576020, compound

HRID 1797270Notes

Reaction equation

HRID 1797270 reaction equation
C(OC(=O)[NH:10][C@H:11]([CH2:27][NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:12][N:13]1[CH2:18][CH2:17][CH:16]([O:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH2:15][CH2:14]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[C:32]([O:31][C:29](=[O:30])[NH:28][CH2:27][C@@H:11]([NH2:10])[CH2:12][N:13]1[CH2:14][CH2:15][CH:16]([O:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH2:17][CH2:18]1)([CH3:35])([CH3:33])[CH3:34]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68577444HCID 68577444, compound

Product 1

HCID 68576020HCID 68576020, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of {(R)-1-(tert-butoxycarbonylamino-methyl)-2-[4-(4-fluoro-phenoxy)-piperidin-1-yl]-ethyl}-carbamic acid benzyl ester (0.88 g, 1.77 mmol) and ammonium formate (0.33 g, 5.31 mmol) in methanol is treated with 10% palladium on charcoal (0.3 g). The reaction mixture is stirred at ambient temperature for 1 hour under nitrogen and then is filtered and evaporated. The residue is dissolved in ethylacetate and washed with saturated brine. The ethylacetate phase is dried over MgSO4 and evaporated to afford {(R)-2-amino-3-[4-(4-fluoro-phenoxy)-piperidin-1-yl]-propyl}-carbamic acid tert-butyl ester. [MH]+ 368.1.

Workup

  1. filtrationis filtered
  2. customevaporated
  3. dissolutionThe residue is dissolved in ethylacetate
  4. washwashed with saturated brine
  5. dry with materialThe ethylacetate phase is dried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-7ed4e96fef5240279a006c113acd7f87
Source dataset
uspto-grants-2006_04
Patent number
US07034042B2

Reaction notes

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