Phenol → HCID 68713043, compound

HRID 451873

Reaction equation

HRID 451873 reaction equation
[Si:1]([O:8][CH2:9][CH:10]1[CH2:12][N@@:11]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:20]1([OH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])([O-])=O.[K+].[K+]>>[Si:1]([O:8][CH2:9][C@@H:10]([NH:11][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:12][O:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 72525716(S)-tert-butyl 2-(t-butyldimethylsilyloxymethyl)aziridine-1-carboxylate

Product 1

HCID 68713043HCID 68713043, compoundYield 30%

Procedure

(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)aziridine-1-carboxylate (5.0 g, 17.4 mmol), phenol (4.92 g, 52.3 mmol), K2CO3 (24 g, 174 mmol) and 150 mL of acetonenitrile were mixed, and heated to reflux for 48 h. The mixture was filtrated, and the filtrate was concentrated in vacuo. The residue was dissolved in 100 mL of EA, which was washed with water (50 mL×2), brine (50 mL) and dried with Na2SO4. The solution was concentrated in vacuo to give crude product, which was purified with flash column to give (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-phenoxypropan-2-ylcarbamate (2.0 g, 5.2 mmol, yield 30%) 1H NMR (CDCl3, 400 MHz) δ 0.0 (s, 6H), 0.87 (s, 9H), 1.45 (s, 9H), 3.71 (dd, 1H), 3.85 (dd, 1H), 3.98 (d, 2H), 4.05 (s, 1H), 6.93 (m, 3H), 7.28 (m, 2H). MS ESI +ve m/z 382 (M+1).

Workup

  1. temperatureheated
  2. temperatureto reflux for 48 h
  3. filtrationThe mixture was filtrated
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved in 100 mL of EA
  6. washwhich was washed with water (50 mL×2), brine (50 mL)
  7. dry with materialdried with Na2SO4
  8. concentrationThe solution was concentrated in vacuo
  9. customto give crude product, which
  10. customwas purified with flash column

Sources & evidence

ORD record
ord-86c75eea12284324bc06835ca933da1c
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Linked notes

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