HCID 5098631, compound → HCID 69419630, compound

HRID 916169Notes

Reaction equation

HRID 916169 reaction equation
[C:1]([NH:4][C:5]1S[C:8]2[CH2:10][CH:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:12][CH2:13][C:7]=2[C:6]=1[C:18]([O:20][CH3:21])=[O:19])(=[O:3])[CH3:2]>[Ni]>[CH3:21][O:20][C:18](=[O:19])[CH:6]([CH:7]1[CH2:13][CH2:12][CH:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:10][CH2:8]1)[CH2:5][NH:4][C:1](=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 5098631HCID 5098631, compound

Product 1

HCID 69419630HCID 69419630, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

Methyl 2-acetamido-6-tert-butyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (0.8286 g, 2.68 mmol) was reductively desulfurized using Raney nickel to yield the title compound as a sticky white solid (0.7466 g, 2.63 mmol, 98.3%); mp: 73-75° C.; TLC: Rf=0.70 (Solvent I), 0.33 (Solvent J); IR (cm−1): 3261 (NH), 2943 (CH aliphatic), 1735 (ester C═O), 1648 (amide C═O), 1H nmr (CDCl3): δ 5.88 (br s, 1H), 3.69 (s, 3H), 3.53 (m, 1H), 3.41 (m, 1H), 3.34 (m, 1H), 2.44 (m, 1H), 1.94 (s, 3H), 1.77 (m, 2H), 1.63 (m, 1H), 1.50 (m, 1H), 1.27 (t, 1H, J=7.1 Hz), 1.00 (m, 4H), 0.82 (s, 9H).

Sources & evidence

ORD record
ord-1efa3f5d4fd54f00b269272efb6459bf
Source dataset
uspto-grants-2007_09
Patent number
US07268164B2

Reaction notes

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