benzyl((1R,2S)-2-{[((2RS)-6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl)(methyl)amino]methyl}cyclohexyl)carbamate → N-(2RS)-{[(1S,2R)-2-aminocyclohexyl]methyl}-6-fluoro-N-methyl-1,2,3,4-tetrahydronaphthalen-2-amine

HRID 1592341Notes

Reaction equation

HRID 1592341 reaction equation
C(OC(=O)[NH:10][C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[CH2:17][N:18]([CH:20]1[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([F:30])[CH:26]=2)[CH2:21]1)[CH3:19])C1C=CC=CC=1>[Pd].CO>[NH2:10][C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[CH2:17][N:18]([CH3:19])[CH:20]1[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([F:30])[CH:26]=2)[CH2:21]1

Participants

4

Reactant 1

HCID 131726669benzyl((1R,2S)-2-{[((2RS)-6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl)(methyl)amino]methyl}cyclohexyl)carbamate

Product 1

HCID 69426330N-(2RS)-{[(1S,2R)-2-aminocyclohexyl]methyl}-6-fluoro-N-methyl-1,2,3,4-tetrahydronaphthalen-2-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl((1R,2S)-2-{[((2RS)-6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl)(methyl)amino]methyl}cyclohexyl)carbamate (280 mg, 0.66 mmol), methanol (20 mL) and 10% palladium on charcoal (56 mg) was shaken under a hydrogen atmosphere (55 psig) for 3.5 hours. The mixture was filtered, the solids were washed with methanol and the filtrate was concentrated under vacuum. The residue (110 mg, 57%) was used without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solids were washed with methanol
  3. concentrationthe filtrate was concentrated under vacuum
  4. customThe residue (110 mg, 57%) was used without further purification

Sources & evidence

ORD record
ord-1565c1d50b9b4673bc12991579ff7618
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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