Water → HCID 59688513, compound

HRID 2267614Notes

Reaction equation

HRID 2267614 reaction equation
[OH:1][CH2:2][C@@H:3]([N:10]([CH3:22])[C:11]([CH:13]1[CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Mg+2].[I-].[I-].[Cl-].[NH4+].O>C1(C)C=CC=CC=1>[OH:14][C@@H:13]1[C@@H:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:1][CH2:2][C@@H:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:10]([CH3:22])[C:11]1=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 5462737Magnesium diiodideHCID 86604632HCID 86604632, compound

Product 1

HCID 59688513HCID 59688513, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of (2RS,3RS)—N-[(1S)-2-hydroxy-1-phenylethyl]-N-methyl-3-phenyloxirane-2-carboxamide (30a) (1.7 g, 5.72 mmol) in anhydrous toluene (120 mL) was added MgI2 (1.6 g, 5.72 mmol, 98% purity) and the mixture vigorously stirred at RT for 32 h. The mixture was treated with saturated ammonium chloride (50 mL) and water (50 mL) and stirred for 30 min. The separated organic layer was washed consecutively with saturated ammonium chloride and brine, dried, filtered and evaporated to an orange oil (1.6 g). Isocratic flash column chromatography (2:1 hexanes-ethyl acetate) separated the title compound (33b) (400 mg, 24%) as a white solid from the (3S,6S,7R) diastereomer (1.0 g, 59%). There was a significant NOE observed between proton 3 and proton 7. HPLC: 1.78 min (Method A).

Workup

  1. stirringstirred for 30 min
  2. washThe separated organic layer was washed consecutively with saturated ammonium chloride and brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated to an orange oil (1.6 g)
  6. customIsocratic flash column chromatography (2:1 hexanes-ethyl acetate) separated the title compound (33b) (400 mg, 24%) as a white solid from the (3S,6S,7R) diastereomer (1.0 g, 59%)
  7. custom1.78 min (Method A)

Sources & evidence

ORD record
ord-f37b2e9eda9548d2ab1d4aaab999f3d8
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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