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

HRID 1592338Notes

Reaction equation

HRID 1592338 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][NH:18][CH:19]1[CH2:28][CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([F:29])[CH:25]=2)[CH2:20]1)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][NH:18][CH:19]1[CH2:28][CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([F:29])[CH:25]=2)[CH2:20]1

Participants

4

Reactant 1

HCID 131726668benzyl((1R,2S)-2-{[((2RS)-6-fluoro-1,2,3,4-tetrahydronaphthalen-2-yl)amino]methyl}cyclohexyl)carbamate

Product 1

HCID 69423061N-{[(1S,2R)-2-aminocyclohexyl]methyl}-(2RS)-6-fluoro-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)amino]methyl}cyclohexyl)carbamate (280 mg, 0.68 mmol) and 10% palladium on charcoal (56 mg) in methanol (20 mL) was shaken under an atmosphere of hydrogen (55 psig) for 3.5 hours. The mixture was filtered, the solid was washed with methanol, and the filtrates were concentrated. The residual oil (120 mg, 64%) was used without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid was washed with methanol
  3. concentrationthe filtrates were concentrated
  4. customThe residual oil (120 mg, 64%) was used without further purification

Sources & evidence

ORD record
ord-6015eba6a66c4e2bb138486ca66bb2aa
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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