HCID 86639081, compound → 1-(4-iodo-2-nitrophenyl)-2-methyl-1-propyl (1S)-camphanate

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Reaction Steps

(R or S)-1-(4-Iodo-2-nitrophenyl)-2,2-dimethyl-1-propyl (1S)-camphanate: (RS)-1-(4-Iodo-2-nitrophenyl)-2,2-dimethyl-1-propyl (1S)-camphanate (2.07 g) was dissolved in boiling methanol (100 mL) and left at room temperature for two days. Crystals formed were filtered to yield pure single diastereomer (R or S)-1-(4-iodo-2-nitrophenyl)-2-methyl-1-propyl (1S)-camphanate (0.409 g, 39%). The absolute configuration of the single diastereomer camphanate is not determined. 1H NMR (400 MHz, CDCl3): δ 8.23 (d, 1 H, J=2.0 Hz, Ph-H), 7.89 (dd, 2 H, J=2.0 and 8.4 Hz, Ph-H), 7.30 (d, 1 H, J=8.4 Hz, Ph-H), 6.56 (s, 1 H, Ph-CH), 2.42 (m, 1 H), 2.07 (m, 1 H), 1.94 (m, 1 H), 1.73 (m, 1 H), 1.11, 1.04 and 0.87 (3 s, 9 H, CH3 3), 0.95 (s, 9 H, (CH3)3C).

Provenance & Evidence