HCID 86705248, compound → HCID 86705250, compound

HRID 879203Notes

Reaction equation

HRID 879203 reaction equation
[CH3:1][O:2][C@H:3]1[C@H:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:7]=[C:6]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][C:18]=2[N+:23]([O-])=O)[CH2:5][C@@H:4]1[CH3:26]>CCO.[Pd]>[NH2:23][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:17]=1[C@@H:6]1[CH2:7][C@H:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[C@@H:3]([O:2][CH3:1])[C@H:4]([CH3:26])[CH2:5]1.[NH2:23][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:17]=1[C@H:6]1[CH2:7][C@@H:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[C@H:3]([O:2][CH3:1])[C@@H:4]([CH3:26])[CH2:5]1

Participants

5

Reactant 1

HCID 86705248HCID 86705248, compound

Product 2

HCID 86705250HCID 86705250, compoundYield 15%HCID 86705251HCID 86705251, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (+/−)-tert-butyl ((1R,5S,6R)-6-methoxy-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-en-1-yl)carbamate (1.0 equiv.) in degassed EtOH (0.10 M) was added Pd/C (0.1 equiv.). The mixture was purged with H2, and allowed to to stir under an atm of H2 overnight at RT. The reaction was filtered through a pad of celite and the cake was washed with MeOH. The organics were concentrated and purified by ISCO SiO2 chromatography. Purification was completed via SFC (30% MeOH, 100 mL/min, AD column) to yield tert-butyl ((1S,2S,3R,5S)-5-(3-aminopyridin-4-yl)-2-methoxy-3-methylcyclohexyl)carbamate (15% yield, 99% ee) and tert-butyl ((1R,2R,3S,5R)-5-(3-aminopyridin-4-yl)-2-methoxy-3-methylcyclohexyl)carbamate (12% yield, 99% ee). LC/MS (m/z)=336.3 (MH+), Rt=0.58 min.

Workup

  1. customThe mixture was purged with H2
  2. filtrationThe reaction was filtered through a pad of celite
  3. washthe cake was washed with MeOH
  4. concentrationThe organics were concentrated
  5. custompurified by ISCO SiO2 chromatography
  6. customPurification

Sources & evidence

ORD record
ord-497e8d1df6ae4388b52cc950ebb38378
Source dataset
uspto-grants-2015_03
Patent number
US08987457B2

Reaction notes

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