Water → HCID 178461668, compound

HRID 628595Notes

Reaction equation

HRID 628595 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]C(C)(C)C.[C:13]1([C@@H:19]([N@:21]2[CH2:23][CH:22]2[CH:24]=[O:25])[CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>C1COCC1>[C:2]1([C@H:24]([CH:22]2[CH2:23][N@@:21]2[C@H:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:20])[OH:25])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7961BromobenzeneHCID 178418306HCID 178418306, compoundHCID 178461670HCID 178461670, compound2×

Product 1

HCID 178461668HCID 178461668, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of bromobenzene (4.93 g, 31.4 mmol) in THF 125 mL under nitrogen at −78° was added t-BuLi (1.7 M in pentane, 50 mL). The mixture was stirred for 0.5 h at room temperature. The mixture was cooled down to −78° C. and a solution of (R)-1-((S)-1-phenylethyl)aziridine-2-carbaldehyde EBE 06048 (2.5 g, 14.3 mmol) in THF (16.7 mL) at −78° C. was added dropwise. The reaction mixture was treated with H2O (20 mL), the organic layer was separated and the aqueous phase was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give a residue that was purified by column chromatography using a gradient of 0-20% [v/v] EtOAc in cyclohexane to give (R)-phenyl((R)-1-((S)-1-phenylethyl)aziridin-2-yl)methanol EBE 06066 (3.13 g, 86% yield).

Workup

  1. temperatureThe mixture was cooled down to −78° C.
  2. customthe organic layer was separated
  3. extractionthe aqueous phase was extracted with EtOAc
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a residue that
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-c7a9b9b674cc4ec0bbb642efb13cf5d3
Source dataset
uspto-grants-2016_04
Patent number
US09314466B2

Reaction notes

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