HCID 178453929, compound → HCID 178453930, compound

HRID 711945Notes

Reaction equation

HRID 711945 reaction equation
[CH3:1][S:2]([CH:5]=[CH:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:9][CH2:8]1)(=[O:4])=[O:3]>[Pd].CO>[CH3:1][S:2]([CH2:5][CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH2:9][CH2:8]1)(=[O:3])=[O:4]

Participants

4

Reactant 1

HCID 178453929HCID 178453929, compound

Product 1

HCID 178453930HCID 178453930, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl {trans-4-[2-(methylsulfonyl)vinyl]cyclohexyl}carbamate (140 mg, 0.46 mmol) and 10% of palladium on carbon (49 mg) in methanol (4 mL) was hydrogenated under balloon pressure of H2 at room temperature overnight. The reaction mixture was filtered and the filtrate was concentrated to give tert-butyl {trans-4-[2-(methylsulfonyl)ethyl]cyclohexyl}carbamate. LCMS calculated for C9H20NO2S (M-Boc+2H)+: m/z=206.1. Found: 206.1. The Boc-intermediate was treated with trifluoroacetic acid (0.2 mL, 3 mmol) in methylene chloride (0.5 mL) at room temperature for 1 h. The resulting mixture was concentrated to give the desired product as trifluoroacetic acid (TFA) salt. LCMS calculated for C9H20NO2S (M+H)+: m/z=206.1. Found: 206.1.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-78b53bc63df141a5a8c1506e26e5bc47
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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