HCID 86704464, compound → HCID 86704462, compound

HRID 1754407Notes

Reaction equation

HRID 1754407 reaction equation
[ClH:1].[F:2][C:3]1([F:23])[CH2:11][N:10]2[C@H:5]([CH2:6][CH:7]([NH:14][C@H](C3C=CC=CC=3)C)[CH2:8][C:9]2([CH3:13])[CH3:12])[CH2:4]1.[H][H]>CO>[ClH:1].[F:23][C:3]1([F:2])[CH2:11][N:10]2[C@H:5]([CH2:6][CH:7]([NH2:14])[CH2:8][C:9]2([CH3:13])[CH3:12])[CH2:4]1

Participants

4

Reactant 2

HCID 86704464HCID 86704464, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86704462HCID 86704462, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A MeOH (20 ml) solution of (8aR)-2,2-difluoro-octahydro-5,5-dimethyl-N—((S)-1-phenylethyl)indolizin-7-amine hydrogen chloride and Pd(OH)2—C (20% on activated carbon, 50% wet, 0.2 g) was hydrogenated in a Parr flask under 45 psi of hydrogen. Additional Pd(OH)2—C was added (˜0.2 g) was added at 16 hours and 24 hours, and the reaction went to completion at 39 hours monitored by LC-MS. Solid was removed by filtration through a short Celite column, washing with MeOH. Filtrate was collected, solvent was removed in vacuo. Compound (8aR)-2,2-difluoro-octahydro-5,5-dimethylindolizin-7-amine hydrogen chloride was obtained as an off-white solid and was used directly in next reaction: 0.56 g; LRMS] (M+H) m/z 204.99.

Workup

  1. additionwas added at 16 hours and 24 hours
  2. customSolid was removed by filtration through a short Celite column
  3. washwashing with MeOH
  4. customFiltrate was collected
  5. customsolvent was removed in vacuo

Sources & evidence

ORD record
ord-406efef817894c14a40bdf7051667cdf
Source dataset
uspto-grants-2015_10
Patent number
US09169249B2

Reaction notes

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