4-Methylmorpholine → HCID 58566698, compound

HRID 1909566Notes

Reaction equation

HRID 1909566 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:6][C:5]2[CH:7]=[C:8]([N:14]3[CH:18]=[N:17][N:16]=[N:15]3)[CH:9]=[C:10]([C:11](O)=[O:12])[C:4]=2[O:3]1.CN1CCOCC1.C(OC(Cl)=O)C(C)C.[BH4-].[Na+]>O.O1CCCC1>[CH3:1][C:2]1([CH3:19])[CH2:6][C:5]2[CH:7]=[C:8]([N:14]3[CH:18]=[N:17][N:16]=[N:15]3)[CH:9]=[C:10]([CH2:11][OH:12])[C:4]=2[O:3]1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 58566438HCID 58566438, compound

Product 1

HCID 58566698HCID 58566698, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,2-dimethyl-5-(1H-tetrazol-1-yl)-2,3-dihydrobenzofuran-7-carboxylic acid (677) (135 mg, 0.519 mmol), N-methylmorpholine (57 μL, 0.519 mmol), and tetrahydrofuran (10 mL) at 0° C. was added isobutylchloroformate (68 μL, 0.519 mmol) and stirred for 2 hours. Sodium borohydride (58.9 mg, 1.56 mmol) in water (3 mL) was added and stirred for 1 hour and at room temperature for an additional 1 hour. The reaction was concentrated in vacuo and water was added. The aqueous phase was extracted with ethyl acetate and the combined organic layers dried over sodium sulfate, filtered and concentrated in vacuo. The crude compound was purified by flash column chromatography on silica gel with hexanes and EtOAc (60%) to afford (2,2-dimethyl-5-(1H-tetrazol-1-yl)-2,3-dihydrobenzofuran-7-yl)methanol (678) (77.8 mg, 61%).

Workup

  1. stirringstirred for 1 hour and at room temperature for an additional 1 hour
  2. concentrationThe reaction was concentrated in vacuo and water
  3. additionwas added
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. dry with materialthe combined organic layers dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude compound was purified by flash column chromatography on silica gel with hexanes and EtOAc (60%)

Sources & evidence

ORD record
ord-273f696a688942c79b62d899d78a8bc5
Source dataset
uspto-grants-2013_12
Patent number
US08598374B2

Reaction notes

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