4-Methylmorpholine → HCID 67170241, compound

HRID 1918350Notes

Reaction equation

HRID 1918350 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[C:8]([CH2:11][CH2:12][C:13](O)=[O:14])=[CH:9][CH:10]=1)=[O:4].CN1CCOCC1.C(OC(Cl)=O)C(C)C.[BH4-].[Na+]>C1COCC1.CO>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:25])[F:24])[CH:17]=2)[C:8]([CH2:11][CH2:12][CH2:13][OH:14])=[CH:9][CH:10]=1)=[O:4]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 67170979HCID 67170979, compound

Product 1

HCID 67170241HCID 67170241, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound of step 2 (150 mg, 0.428 mmol) was dissolved in THF. N-methylmorpholine (56 mg, 0.556 mmol) and isobutylchloroformate (70 mg, 0.514 mmol) were added at room temperature. After stirring for 2 minutes, the mixture was filtered and rinsed with THF. Sodium borohydride (65 mg, 1.71 mmol) was added to the filtrate and thereafter slowly methanol until intensive foaming indicated the start of the reaction. After 5 minutes the reaction was complete as indicated by LC-MS analytics. Volatiles were evaporated in vacuo, the remainder was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution, the combined organic extracts were dried over sodium chloride and evaporated to dryness. This raw material was purified by silica gel chromatography with a hetpane/ethyl acetate gradient to yield the title compound (106 mg)

Workup

  1. filtrationthe mixture was filtered
  2. washrinsed with THF
  3. customthe start of the reaction
  4. waitAfter 5 minutes the reaction was complete
  5. customVolatiles were evaporated in vacuo
  6. customthe remainder was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  7. dry with materialthe combined organic extracts were dried over sodium chloride
  8. customevaporated to dryness
  9. customThis raw material was purified by silica gel chromatography with a hetpane/ethyl acetate gradient

Sources & evidence

ORD record
ord-b6cca605027249ce87fde4bedf80ad06
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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