HCID 68907671, compound → 1,1-Dimethylethyl N-[(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate

HRID 459547Notes

Reaction equation

HRID 459547 reaction equation
C(OC([NH:11][C@H:12]1[CH2:17][CH2:16][C@@H:15]([C:18](=[O:22])[N:19]([CH3:21])[CH3:20])[CH2:14][C@@H:13]1[NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=O)C1C=CC=CC=1.[H][H]>O1CCCC1.[Pd]>[C:27]([O:26][C:24]([NH:23][C@@H:13]1[CH2:14][C@@H:15]([C:18](=[O:22])[N:19]([CH3:20])[CH3:21])[CH2:16][CH2:17][C@@H:12]1[NH2:11])=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

5

Reactant 2

HCID 68907671HCID 68907671, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 469135491,1-Dimethylethyl N-[(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl]carbamateYield 97.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(1S,2S,4R)-N1-Benzyloxycarbonyl-N2-(tert-butoxycarbonyl)-4-(N,N-dimethylcarbamoyl)-1,2-cyclohexanediamine (560 mg) was dissolved in tetrahydrofuran (100 ml), and 10% palladium on carbon (220 mg) was added to stir the mixture for 17 hours in a hydrogen atmosphere. After the catalyst was removed by filtration, the filtrate was concentrated to obtain the title compound (370 mg) as a colorless oil.

Workup

  1. customAfter the catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-db5b6d4c498b4d51ba8908557119433e
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

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