Borane → HCID 17989424, compound

HRID 1353090Notes

Reaction equation

HRID 1353090 reaction equation
[N:1]1([C:5](=O)[CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=2[O:17][CH3:18])[CH2:4][CH2:3][CH2:2]1.B>C1COCC1>[CH3:18][O:17][C:9]1[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:8]=1[O:7][CH2:6][CH2:5][N:1]1[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6331BoraneHCID 17989370HCID 17989370, compound

Product 1

HCID 17989424HCID 17989424, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

This amide was dissolved in THF (15 ml) then borane (5.6 ml, 1M solution in THF) was introduced. The reaction mixture was stirred for 18 hours at 50° C. under argon. Excess borane was quenched by the dropwise addition of MeOH then aq HCl (2M, 200 ul). The solvent was removed in vacuo and the residual oil partitioned between ethyl acetate and a saturated solution of aqueous sodium bicarbonate (20 ml). The aqueous phase was extracted with ethyl acetate (3×50 ml). The combined ethyl acetate layers were washed with brine and dried over MgSO4. The solvent was removed in vacuo to yield 1-[2-(2-methoxy-4-nitro-phenoxy)-ethyl]-azetidine as a pale red oil (53 mg, 38%);

Workup

  1. customExcess borane was quenched by the dropwise addition of MeOH
  2. customThe solvent was removed in vacuo
  3. customthe residual oil partitioned between ethyl acetate
  4. extractionThe aqueous phase was extracted with ethyl acetate (3×50 ml)
  5. washThe combined ethyl acetate layers were washed with brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-927a2445ebb74c4fa7fec9df68c1d90f
Source dataset
uspto-grants-2007_05
Patent number
US07220777B2

Reaction notes

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