HCID 59305171, compound → HCID 59305202, compound

HRID 1971149Notes

Reaction equation

HRID 1971149 reaction equation
[CH3:1][CH:2]1[C:7]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH2:8]2)[CH2:6][CH2:5][N:4](CC2C=CC=CC=2)[CH2:3]1.[H][H]>[Pd].C(O)(=O)C>[CH3:1][CH:2]1[C:7]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH2:8]2)[CH2:6][CH2:5][NH:4][CH2:3]1

Participants

5

Reactant 2

HCID 59305171HCID 59305171, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59305202HCID 59305202, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

3′-Methyl-1′-(phenylmethyl)-1,2-dihydrospiro[indole-3,4′-piperidine] (10 mmol, 2.9 g), acetic acid (30 mL) and Pd/C (5%, 600 mg) were added to a Parr bottle. The mixture was subjected to hydrogen gas at 30 psi for 20 h, after which time the solution was filtered over celite, concentrated and purified by reverse phase chromatography, 10-50% acetonitrile/water (0.1% TFA) over 14 min to give 3′-methyl-1,2-dihydrospiro[indole-3,4′-piperidine] (750 mg) as the TFA salt as an off white solid. MS (ES) m/e 203 [M+H]+ 1H NMR (400 MHz, DMSO-d6) δ ppm 0.62 (d, J=7.03 Hz, 3H) 1.83 (d, J=14.31 Hz, 1H) 2.00 (td, J=13.87, 4.14 Hz, 1H) 2.13 (dd, J=7.15, 4.39 Hz, 1H) 2.77 (d, J=11.80 Hz, 1H) 2.94 (d, J=11.54 Hz, 1H) 3.17 (d, J=1.51 Hz, 1H) 3.31 (d, J=13.30 Hz, 1H) 3.40 (d, J=10.79 Hz, 1H) 3.61 (d, J=11.04 Hz, 1H) 6.79 (d, J=7.78 Hz, 1H) 6.88 (t, J=7.28 Hz, 1H) 7.03 (d, J=7.28 Hz, 1H) 7.12 (t, J=7.15 Hz, 1H) 8.74 (br. s., 1H) 8.87 (br. s. 1H).

Workup

  1. filtrationafter which time the solution was filtered over celite,
  2. concentrationconcentrated
  3. custompurified by reverse phase chromatography, 10-50% acetonitrile/water (0.1% TFA) over 14 min

Sources & evidence

ORD record
ord-51e076192e9e4eca881309c8312cb145
Source dataset
uspto-grants-2013_04
Patent number
US08431590B2

Reaction notes

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