N-Iodosuccinimide → HCID 86755238, compound

HRID 1637049Notes

Reaction equation

HRID 1637049 reaction equation
[CH2:1]([N:10]([C@@H:27]([CH3:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C@@H:11]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C@H:12]([OH:20])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.IN1C(=[O:41])CCC1=O>>[C:1]([N:10]([C@@H:27]([CH3:34])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C@@H:11]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C@H:12]([OH:20])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])(=[O:41])[CH:2]=[CH:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 120273N-IodosuccinimideHCID 86755239HCID 86755239, compound

Product 1

HCID 86755238HCID 86755238, compoundYield 45%

Procedure

Compound (28) from Example 13 (0.200 g, 0.44 mmol) was treated with N-iodosuccinimide (0.197 g, 0.88 mmol) using standard iodoetherification conditions. Flash chromatography of the product on silica gel [ethyl acetate/petroleum (1:9)] afforded the title compound (54) (Rf 0.50) as a yellow oil (0.093 g, 45%). δH (200 MHz; CDCl3) 7.72 (1H, d, J=16.0, CH=CHPh), 7.57-7.22 (15H, m, Ph), 6.51 (1H, d, J=16.0, PhCH=CH), 5.45 (1H, d, J=4.9, CHCHOH), 4.25 (1H, d, J=4.9, PhCHCH), 3.81 (1H, d, J=6.5, PhCHCH3), 1.92 (1H, br s, OH), 1.34 (3H, d, J=6.5, PhCHCH3), 1.32 (9H, s, (CH3)3C). The corresponding 3-(α-methylbenzylamino) derivative (Rf 0.25) was also recovered as a colourless oil (0.045 g, 30%. δH (200 MHz; CDCl3) 7.48-7.14 (10H, m, Ph), 4.50 (1H, d, J=3.8, CHCHOH), 4.09 (1H, d, J=3.8, PhCHCH), 3.76 (1H, q, J=6.6, PhCHCH3), 1.38 (3H, d, J=6.6, PhCHCH3), 1.31 (9H, s, (CH3)3C).

Sources & evidence

ORD record
ord-23fe17e79be64481b84d7d8204aae7b1
Source dataset
uspto-grants-2000_03
Patent number
US06037498

Reaction notes

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