Ethanol → HCID 15232314, compound

HRID 1742378Notes

Reaction equation

HRID 1742378 reaction equation
[C:1]1([CH:7]=[C:8]2[CH2:14][CH:13]3[NH:15][CH:10]([CH2:11][CH2:12]3)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:16]([Si:19]([CH:35]([CH3:37])[CH3:36])([CH:32]([CH3:34])[CH3:33])[O:20][C:21](Br)([CH3:30])[C:22]([C:24]1C=CC=CC=1)=O)([CH3:18])[CH3:17].C(N([CH2:43][CH3:44])CC)C.[CH3:45]COCC.[CH2:50]([OH:52])[CH3:51]>>[C:1]1([CH:7]=[C:8]2[CH2:14][CH:13]3[N:15]([CH:43]([CH3:44])[C:50]([C:51]4[CH:24]=[CH:22][C:21]([O:20][Si:19]([CH:16]([CH3:17])[CH3:18])([CH:32]([CH3:33])[CH3:34])[CH:35]([CH3:36])[CH3:37])=[CH:30][CH:45]=4)=[O:52])[CH:10]([CH2:11][CH2:12]3)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 3283Diethyl EtherHCID 8471TriethylamineHCID 15337559HCID 15337559, compoundHCID 131718643HCID 131718643, compound

Product 1

HCID 15232314HCID 15232314, compoundYield 23%

Procedure

A mixture of 3-phenylmethylene-8-azabicyclo[3.2.1]octane (1.09 g, 4.87 mmol), 4-(triisopropylsiloxy-alpha-bromopropiophenone (1.88 g, 4.88 mmol) and triethylamine (1.5 ml, 10.76 mmol) in ethanol (75 ml) was refluxed 22 hours. After cooling, ether (50 ml) was added and the mixture was filtered through diatomaceous earth. The filtrate was concentrated and chromatographed on silica gel (2×6 inches, hexane then ethyl acetate/hexane gradient) to give 0.56 g (23%) of an orange oil product; NMR 8.18 (d, 2H), 7.25 (t, 2H), 7.12 (d, 3H), 6.86 (d, 2H), 6.29 (s, 1H), 4.08 (m, 1H), 3.47-3.26 (m, 2H), 2.75 (m, 1H), 2.57-2.37 (m, 2H), 2.03-1.72 (m, 4H), 1.6 (m, 1H; partially under water peak from NMR solvent), 1.40 (d, 3H), 1.25 (m, 3H), 1.09 (d, 18H).

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered through diatomaceous earth
  3. concentrationThe filtrate was concentrated
  4. customchromatographed on silica gel (2×6 inches, hexane

Sources & evidence

ORD record
ord-71721a35c77f48e6b3bd6d3dc3d70264
Source dataset
uspto-grants-1994_08
Patent number
US05338754

Reaction notes

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