HCID 86596964, compound → HCID 69285451, compound

HRID 2225286Notes

Reaction equation

HRID 2225286 reaction equation
[C:1]([NH:5][C@@H:6]1[CH2:11][CH2:10][C@H:9]([NH:12]C(=O)OCC2C=CC=CC=2)[C@H:8]([CH2:23][S:24]([CH:27]([CH3:29])[CH3:28])(=[O:26])=[O:25])[CH2:7]1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([NH:5][C@@H:6]1[CH2:11][CH2:10][C@H:9]([NH2:12])[C@H:8]([CH2:23][S:24]([CH:27]([CH3:29])[CH3:28])(=[O:25])=[O:26])[CH2:7]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86596964HCID 86596964, compound

Product 1

HCID 69285451HCID 69285451, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of benzyl (1S,2R,4R)-4-(tert-butylamino)-2-(isopropylsulfonylmethyl)-cyclohexylcarbamate (230 mg, 0.54 mmol), in 50 mL of MeOH was treated with 50 mg of 10% Pd/C and hydrogenated overnight at 55 psi. The mixture was filtered through Celite and concentrated on a rotary evaporator to give 150 mg of (1R,3R,4S)-N1-tert-butyl-3-(isopropylsulfonylmethyl)cyclohexane-1,4-diamine. This was used without further purification.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-476a7b1038b3407e8fe85fff81fd63dc
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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