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

HRID 1499652Notes

Reaction equation

HRID 1499652 reaction equation
[C@:1]12([CH3:28])[C:7]([CH3:9])([CH3:8])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[C:10]([O:12][CH:13]([C:18]1[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=1[N+:25]([O-:27])=[O:26])[C:14](C)([CH3:16])[CH3:15])=[O:11]>CO>[C@:1]12([CH3:28])[C:7]([CH3:9])([CH3:8])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[C:10]([O:12][CH:13]([C:18]1[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=1[N+:25]([O-:27])=[O:26])[CH:14]([CH3:15])[CH3:16])=[O:11]

Participants

3

Reactant 1

HCID 86639081HCID 86639081, compound2×

Product 1

HCID 866390821-(4-iodo-2-nitrophenyl)-2-methyl-1-propyl (1S)-camphanateYield 39%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(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).

Workup

  1. customCrystals formed
  2. filtrationwere filtered

Sources & evidence

ORD record
ord-9724c3a71f5942908ab55e20fc18ff3e
Source dataset
uspto-grants-2015_12
Patent number
US09200319B2

Reaction notes

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