HCID 57608435, compound → HCID 57956716, compound

HRID 1021084Notes

Reaction equation

HRID 1021084 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:11]#[C:12][C:13]2([OH:19])[CH2:18][CH2:17][S:16][CH2:15][CH2:14]2)[CH:8]=[CH:9][CH:10]=1>CCOC(C)=O.CO>[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[CH2:11][CH2:12][C:13]1([OH:19])[CH2:14][CH2:15][S:16][CH2:17][CH2:18]1

Participants

3

Reactant 1

HCID 57608435HCID 57608435, compound

Product 1

HCID 57956716HCID 57956716, compound

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

Hydrogenation of 4-((3-(2-aminoethoxy)phenyl)ethynyl)tetrahydro-2H-thiopyran-4-ol was conducted following the method used to prepare Example 2 except that EtOAc-MeOH (90%) was used as the reaction solvent. Example 11 was isolated as a colorless oil. Yield (0.179 g, 98%): 1H NMR (400 MHz, DMSO-d6) δ 7.13 (t, J=8 Hz, 1H), 6.34-6.88 (m, 3H), 4.26 (br s, 1H), 3.86 (t, J=6.0 Hz, 2H), 2.57-2.88 (m, 4H), 2.53-2.56 (m, 2H), 2.32-2.37 (m, 2H), 1.73-1.78 (m, 2H), 1.42-1.62 (m, 6H).

Workup

  1. customExample 11 was isolated as a colorless oil
  2. customYield (0.179 g, 98%)

Sources & evidence

ORD record
ord-70970cd7c4734f1b9391f467aac4d991
Source dataset
uspto-grants-2014_05
Patent number
US08716529B2

Reaction notes

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