Tetrahydrofuran → HCID 69247048, compound

HRID 2371114Notes

Reaction equation

HRID 2371114 reaction equation
[C:1]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9](=[O:31])[CH:10]([CH2:18][CH2:19][N:20]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]2=[O:30])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:3][CH:2]=1.C1COCC1.[BH4-].[Na+]>CO>[C:1]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH:9]([OH:31])[CH:10]([CH2:18][CH2:19][N:20]2[C:21](=[O:30])[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:28]2[OH:29])[C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 66671335HCID 66671335, compound

Product 1

HCID 69247048HCID 69247048, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the compound (165 mg) prepared from Step 1 above, in dry methanol and THF (1:1, 8 ml) at −20° C. was added sodium borohydride (38 mg) and the reaction mixture was stirred at rt for 3 h and then at 45° C. for 1 hour. The reaction mixture was cooled to 0° C. and quenched with saturated ammonium chloride solution. The solvents were evaporated in vacuo and the residue taken into water and extracted with ethyl acetate. The combined organic extracts were washed with water and brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain the crude title compound (165 mg).

Workup

  1. waitat 45° C. for 1 hour
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. customquenched with saturated ammonium chloride solution
  4. customThe solvents were evaporated in vacuo
  5. extractionextracted with ethyl acetate
  6. washThe combined organic extracts were washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-78c3766bdcb343beb77a26cecf089d32
Source dataset
uspto-grants-2014_04
Patent number
US08710261B2

Reaction notes

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