N,N,N',N'-Tetramethylethylenediamine → HCID 10646230, compound

HRID 1019287Notes

Reaction equation

HRID 1019287 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:18]=[C:17]([O:19][CH2:20][O:21][CH3:22])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(CCN(C)C)C.[Li]CCCC.ClCC[I:39]>C1COCC1.CCCCCC.O.[Au]>[C:1]([O:5][C:6]([NH:8][C:9]1[C:18]([I:39])=[C:17]([O:19][CH2:20][O:21][CH3:22])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 1364381-Chloro-2-iodoethaneHCID 10828268N-(tert-Butyloxycarbonyl)-4-(methoxymethoxy)-2-naphthylamineHCID 178418339Butyllithium

Product 1

HCID 10646230HCID 10646230, compoundYield 80%

Reagents, catalysts & solvents 4

HCID 23985GoldCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 23 (0.435 g 1.43 mmol) in 5.7 mL anhydrous THF was cooled to −25° C. and treated with TMEDA (0.758 mL, 5.0 mmol) followed by n-BuLi (2.29 mL of a 2.5 M solution in hexane, 5.0 mmol) in a slow dropwise manner. The resulting gold solution was stirred for 2 h at −25° C. The reaction mixture was treated with 1-chloro-2-iodoethane (0.37 mL, 5.0 mmol) and stirred for 15 min at 25° C. The reaction was diluted with H2O (40 mL), extracted with Et2O (3×20 mL), and the combined organic extracts were washed with saturated aqueous NaCl, dried Na2SO4) and concentrated under reduced pressure. Flash chromatography (SiO2, 2.5×15 cm, 0-7% EtOAc/hexane gradient) yielded 24 (490 mg, 80%) as a yellow oil: 1H NMR (CDCl3, 400 MHz) δ 8.35 (s, 1H), 8.03 (d, J=12.8 Hz, 1H), 7.78 (d, J=12.5 Hz, 1H), 7.42 (m, 2H), 7.14 (br s, 1H), 5.20 (s, 2H), 3.74 (s, 3H), 1.56 (s, 9H); 13C NMR (CDCl3, 100 MHz) δ 154.7, 152.6, 135.1, 134.8, 127.6, 127.4, 125.1, 125.0, 122.2, 113.0, 100.5, 87.7, 81.1, 58.5, 28.4; IR (film) νmax 3391, 2977, 2933, 1732, 1524, 1367, 1340, 1276, 1228, 1157 cm−1; FABHRMS (NBA/NaI) m/z 430.0507 (C17H20INO4+H+ requires 430.0515).

Workup

  1. extractionextracted with Et2O (3×20 mL)
  2. washthe combined organic extracts were washed with saturated aqueous NaCl, dried Na2SO4) and
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3b52fb9cde21437aa92e5551375306dc
Source dataset
uspto-grants-2002_11
Patent number
US06486326B2

Reaction notes

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