Imidazole → (S)-2-(7-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-tert-butoxyethyl pivalate

HRID 926164Notes

Reaction equation

HRID 926164 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:21])[C:8]([C@H:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:14][OH:15])=[C:9]2[OH:12])=[CH:4][CH:3]=1.N1C=CN=C1.[C:27](Cl)(=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29].[NH4+].[Cl-]>C(Cl)Cl>[C:27]([O:15][CH2:14][C@H:13]([C:8]1[C:7]([CH3:21])=[CH:6][C:5]2[C:10](=[CH:11][C:2]([Br:1])=[CH:3][CH:4]=2)[C:9]=1[OH:12])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])(=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 62493Pivaloyl chlorideHCID 89676522(S)-7-bromo-2-(1-tert-butoxy-2-hydroxyethyl)-3-methylnaphthalen-1-ol

Product 1

HCID 89676744(S)-2-(7-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-tert-butoxyethyl pivalate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-7-bromo-2-(1-tert-butoxy-2-hydroxyethyl)-3-methylnaphthalen-1-ol (1.84 g, 5.20 mmol) in CH2Cl2 (15 mL) added imidazole (426 mg, 6.25 mmol) and pivalyl chloride (705 μL, 5.7 mmol). The reaction was stirred at room temperature for 36 h. A saturated solution of NH4Cl 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) to give the product. 1H-NMR: 400 MHz, (CDCl3) δ: 8.21 (s, 1H), 7.63 (m, 2H), 7.26 (s, 1H), 5.47 (dd, J=10, 3 Hz, 1H), 4.62 (dd, J=12, 10 Hz, 1H), 4.14 (dd, J=12, 3 Hz, 1H), 2.75 (s, 3H), 1.22 (s, 9H) 1.11 (s, 9H).

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. customto give the product

Sources & evidence

ORD record
ord-2cce1d99d59d493aaaa5b06353c8dbf1
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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