Acetone → HCID 86747094, compound

HRID 1033950Notes

Reaction equation

HRID 1033950 reaction equation
[CH3:1][C:2]([Si:5]([CH3:23])([CH3:22])[O:6][CH2:7][C@@H:8]1[C@@H:11]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C:9]1=O)([CH3:4])[CH3:3].Cl.[O:25]([NH2:27])[CH3:26].CC(C)=O.CCOC(C)=O>N1C=CC=CC=1.CCCCCC>[CH3:26][O:25][N:27]=[C:9]1[CH2:10][C@H:11]([CH2:12][O:13][Si:14]([C:17]([CH3:18])([CH3:20])[CH3:19])([CH3:16])[CH3:15])[C@H:8]1[CH2:7][O:6][Si:5]([C:2]([CH3:3])([CH3:4])[CH3:1])([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 180AcetoneHCID 8857Ethyl AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 10882873HCID 10882873, compound

Product 1

HCID 86747094HCID 86747094, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8058HexaneSolvent

Procedure

A solution of 415.3 g (1.16 mol) of [2S,3S]-2,3-bis(((1,1-dimethylethyl)dimethylsilyl) oxymethyl)cyclobutanone, the product of Step 1D, in 540 mL of pyridine is added to 117 g (1.2 equivalents) of methoxylamine hydrochloride. The reaction mixture was stirred mechanically for 1 hour at ambient temperature and checked by TLC on silica gel eluting with 4% acetone in hexane. The reaction mixture was stirred until the starting material was consumed according to TLC analysis, and then it was concentrated in vacuo. The residue was then diluted with ethyl acetate (1 L) and water (0.5 L). The resultant layers were separated and the aqueous layer was extracted with ethyl acetate. The combined ethyl acetate solution was washed twice with water (250 mL) and once with brine (150 mL), dried over anhydrous magnesium sulfate, filtered and concentrated In vacuo. The residue is purified by flash chromatography on 1 kg silica gel column eluted with 10% diethyl ether in hexane to give 425 g (94% yield) of the title compound, [α]D @25° C.=-25.8° (c 3.36; EtOAc).

Workup

  1. stirringThe reaction mixture was stirred until the starting material
  2. customwas consumed
  3. concentrationit was concentrated in vacuo
  4. additionThe residue was then diluted with ethyl acetate (1 L) and water (0.5 L)
  5. customThe resultant layers were separated
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. washThe combined ethyl acetate solution was washed twice with water (250 mL) and once with brine (150 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated In vacuo
  11. customThe residue is purified by flash chromatography on 1 kg silica gel column
  12. washeluted with 10% diethyl ether in hexane

Sources & evidence

ORD record
ord-a6fd2e2a6619426e941f4e9b89e5f62f
Source dataset
uspto-grants-1994_05
Patent number
US05312963

Reaction notes

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