Methanol → HCID 54303873, compound

HRID 2166012Notes

Reaction equation

HRID 2166012 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[K].[CH3:11][C@@H:12]([CH2:15][CH:16]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH3:17])[CH:13]=O.CO.O>C1COCC1.[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CCC.C1(C)C=CC=CC=1>[CH3:11][CH:12]([CH2:15][C@H:16]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:17]=[CH:11][CH2:12][CH2:15][CH3:16])[CH3:13]

Participants

8

Reactant 4

HCID 887MethanolHCID 962WaterHCID 45051783Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, potassium saltHCID 86744108HCID 86744108, compound

Product 1

HCID 54303873HCID 54303873, compoundYield 173.5%

Reagents, catalysts & solvents 3

HCID 159628Butyltriphenylphosphonium bromideCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Potassium hexamethyldisilazane (10.8 mL of a 1.85M solution in THF, 20 mmol) was added over 15 minutes to a stirred mixture of n-butyl triphenyl-phosphonium bromide (7.99 g., 20 mmol) and THF (75 mL) at 0°. After addition was complete, the mixture was stirred at 0° for 30 minutes and then a solution of (S)-2-methyl-4-(tert. butoxycarbonylamino) pentanal (2.04 g, 9.48 mmol) in toluene (10 mL) was added over 15 minutes. The reaction mixture was stirred at 0° for 30 minutes, 20°-25° for 30 minutes and then at 40° for 18 hours. Methanol (1 mL) then H2O (5 mL) were added and solvents removed under reduced pressure at 40°. The residue was partitioned between ethyl acetate and a dilute solution of Rochelle's salt. The ethyl acetate extract was washed with brine, dried (Na2SO4), filtered and concentrated. Flash chromatography of the residue over silica gel and elution with 10% ethyl acetate 90% hexane gave 2.10 g of product.

Workup

  1. additionAfter addition
  2. stirringThe reaction mixture was stirred at 0° for 30 minutes, 20°-25° for 30 minutes
  3. waitat 40° for 18 hours
  4. customsolvents removed under reduced pressure at 40°
  5. customThe residue was partitioned between ethyl acetate
  6. extractionThe ethyl acetate extract
  7. washwas washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. washFlash chromatography of the residue over silica gel and elution with 10% ethyl acetate 90% hexane

Sources & evidence

ORD record
ord-b397f44964bc4f2e94b076117769f463
Source dataset
uspto-grants-1990_07
Patent number
US04943561

Reaction notes

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