Ammonium formate → HCID 18367245, compound

HRID 1741410Notes

Reaction equation

HRID 1741410 reaction equation
C([NH:8][CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[O:19][Si:20]([C:33]([CH3:36])([CH3:35])[CH3:34])([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:10]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:8][CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[O:19][Si:20]([C:33]([CH3:36])([CH3:35])[CH3:34])([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:10]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 18367270HCID 18367270, compound

Product 1

HCID 18367245HCID 18367245, compoundYield 45.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-benzylamino-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (3.15 g), ammonium formate (4.41 g) and Pd/C (0.15 g) in ethanol (EtOH) (40 ml) was refluxed for 3.5 hours. The insoluble material was filtered off and the solvent was evaporated in vacuo. The residue was partitioned between ethyl acetate and sat. NaHCO3. The organic layer was washed with brine. The dried solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel to give 2-amino-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (1.18 g). FABMS (m/z): 402 (M+ +1) NMR (CDCl3, δ): 1.10 (9H, s), 1.56-1.82 (1H, m), 2.05-2.35 (1H, m), 2.52-2.39 (5H, m), 6.24 (1H, d, J=6.4 Hz), 6.59-6.73 (2H, m), 7.32-7.42 (6H, m), 7.67-7.74 (4H, m)

Workup

  1. temperaturewas refluxed for 3.5 hours
  2. filtrationThe insoluble material was filtered off
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was partitioned between ethyl acetate and sat. NaHCO3
  5. washThe organic layer was washed with brine
  6. customThe dried solvent was evaporated in vacuo
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-bfb3b266c39741a287497750e05b8fbe
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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