Water → (S)-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl) 2-(7-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate

HRID 926162Notes

Reaction equation

HRID 926162 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:28])[C:8]([C@H:13]([OH:27])[C:14]([O:16][C@@H:17]3[CH2:22][C@H:21]([CH3:23])[CH2:20][CH2:19][C@H:18]3[CH:24]([CH3:26])[CH3:25])=[O:15])=[C:9]2[OH:12])=[CH:4][CH:3]=1.Cl(O)(=O)(=O)=O.O>C(OC(C)=O)(C)(C)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:28])[C:8]([C@H:13]([O:27][C:5]([CH3:10])([CH3:6])[CH3:4])[C:14]([O:16][C@@H:17]3[CH2:22][C@H:21]([CH3:23])[CH2:20][CH2:19][C@H:18]3[CH:24]([CH3:25])[CH3:26])=[O:15])=[C:9]2[OH:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24247Perchloric AcidHCID 118023859(S)-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl) 2-(7-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-hydroxyacetate

Product 1

HCID 118023367(S)-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl) 2-(7-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

To a solution of (S)-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl) 2-(7-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-hydroxyacetate in t-BuOAc (150 mL) was added 70% perchloric acid (HClO4) (3.0 mL). After 3 h, water was added. The layers were separated, and the organic layer was dried, filtered, and concentrated in vacuo. The crude material was purified by column chromatography (EtOAc/hexanes). Upon sitting, crystals formed in the resulting oil that were the desired diastereomer. 1H-NMR: 400 MHz, (CDCl3) δ: 9.11 (s, 1H), 8.39 (s, 1H), 7.48 (m, 2H), 7.10 (s, 1H), 5.46 (s, 1H), 4.66 (m, 2H), 2.53 (s, 3H), 1.71 (m, 2H), 1.62 (m, 2H), 1.36 (m, 2H), 1.32 (s, 9H), 0.80 (m, 7H), 0.60 (d, J=6 Hz, 3H).

Workup

  1. customThe layers were separated
  2. customthe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by column chromatography (EtOAc/hexanes)
  6. customcrystals formed in the resulting oil that

Sources & evidence

ORD record
ord-6a99552aa7984376a5a1870c60406379
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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