HCID 57225501, compound → HCID 57021050, compound

HRID 2305217Notes

Reaction equation

HRID 2305217 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C@:18]34[O:24][C@H:19]3[CH2:20][CH2:21][CH2:22][CH2:23]4)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=1)[CH2:30][Mg]Cl>O1CCCC1.[Cu](Br)Br>[C:1]1([C:7]2[N:8]=[C:9]([C@@:18]3([OH:24])[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]3[CH2:30][C:29]3[CH:33]=[CH:34][CH:35]=[C:27]([O:26][CH3:25])[CH:28]=3)[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 57225501HCID 57225501, compoundHCID 178490222HCID 178490222, compound

Product 1

HCID 57021050HCID 57021050, compoundYield 105.4%

Reagents, catalysts & solvents 2

HCID 24611Copper bromide (CuBr2)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (1R,2S)-1-(4,5-diphenyloxazol-2-yl)-1,2-epoxycyclohexane (20 g) and copper bromide (3.0 g) in tetrahydrofuran (400 ml) was dropwise added a solution of 3-methoxybenzylmagnesium chloride [prepared from 3-methoxybenzylchloride (50 g) and Mg (9.2 g)] in tetrahydrofuran (500 ml) at −78° C. under N2. The mixture was stirred for 2 hours at the room temperature and partitioned between EtoAc and water. The organic layer was washed with 1N-hydrochloric acid, water, saturated sodium hydrogencarbonate and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to give (1R,2S)-1-(4,5-diphenyloxazol-2-yl)-1-hydroxy-2-(3-methoxybenzyl)cyclohexane (29.2 g).

Workup

  1. custompartitioned between EtoAc and water
  2. washThe organic layer was washed with 1N-hydrochloric acid, water, saturated sodium hydrogencarbonate and brine
  3. customThe dried solvent was evaporated in vacuo
  4. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-4360e0ca6bfc4700be171a6f8d383de3
Source dataset
uspto-grants-2002_08
Patent number
US06437146B1

Reaction notes

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