Ammonium formate → HCID 178501198, compound

HRID 518599Notes

Reaction equation

HRID 518599 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])=[CH:6][C:5]=1[NH:22][C@@H:23]1[CH2:28][CH2:27][C@H:26]([C:29]([O:31][CH3:32])=[O:30])[CH2:25][CH2:24]1)([O-])=O.C([O-])=O.[NH4+]>CCO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][Si:12]([CH:19]([CH3:21])[CH3:20])([CH:13]([CH3:15])[CH3:14])[CH:16]([CH3:17])[CH3:18])=[CH:6][C:5]=1[NH:22][C@@H:23]1[CH2:24][CH2:25][C@H:26]([C:29]([O:31][CH3:32])=[O:30])[CH2:27][CH2:28]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 178501199HCID 178501199, compound

Product 1

HCID 178501198HCID 178501198, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A round bottom flask under nitrogen atmosphere was charged with cis-methyl 4-(2-nitro-5-((triisopropylsilyloxy)methyl)phenylamino)cyclohexanecarboxylate (2.77 g, 5.96 mmol) and palladium (10% on carbon) (0.634 g, 0.596 mmol). To this was added EtOH (48.5 mL) followed by ammonium formate (3.76 g, 59.6 mmol). The reaction mixture was stirred at RT for 2 hours and then diluted with EtOH and filtered through Celite® brand filter aid. The filter cake was washed sequentially with DCM (100 mL), EtOH (100 mL), and MeOH (100 mL). The filtrate was concentrated, re-diluted with DCM (100 mL) and washed with brine. The organic layer was collected, dried over sodium sulfate and concentrated to afford cis-methyl 4-(2-amino-5-((triisopropylsilyloxy)methyl)phenylamino)cyclohexanecarboxylate as a brown oil (2.58 g, 100% yield). MS m/z=435.2 [M+H]. Calc'd for C24H42N2O3Si: 434.3.

Workup

  1. filtrationfiltered through Celite® brand
  2. filtrationfilter aid
  3. washThe filter cake was washed sequentially with DCM (100 mL), EtOH (100 mL), and MeOH (100 mL)
  4. concentrationThe filtrate was concentrated
  5. additionre-diluted with DCM (100 mL)
  6. washwashed with brine
  7. customThe organic layer was collected
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-21962e4c825341b09ca45c230f914184
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

Loading…