Tributylvinyltin → HCID 58109276, compound

HRID 2037484Notes

Reaction equation

HRID 2037484 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@:13]([CH2:22][CH2:23][CH2:24][OH:25])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:12][C:11]2=[O:26])[CH3:9])=[CH:4][CH:3]=1.[CH2:27]([Sn](CCCC)(CCCC)C=C)[CH2:28]CC>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[OH:25][CH2:24][CH2:23][CH2:22][C@@:13]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:12][C:11](=[O:26])[N:10]([C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([CH:27]=[CH2:28])=[CH:3][CH:4]=2)[CH3:9])[CH2:15][CH2:14]1

Participants

6

Reactant 2

HCID 81998TributylvinyltinHCID 59532368(R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one

Product 1

HCID 58109276HCID 58109276, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A solution of (R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one (200 mg, 0.462 mmol), tributyl-vinyl-stannane (198 mg, 0.624 mmol), Pd2(dba)3 (23 mg, 0.005 mmol) and BINAP (6.84 mg, 0.011 mmol) in toluene (20 mL) was heated to reflux overnight. The reaction mixture was filtered, and the filtrate was concentrated to give the crude product, which was purified by preparative TLC to give (R)-6-(3-hydroxypropyl)-6-phenyl-3-((S)-1-(4-vinylphenyl)ethyl)-1,3-oxazinan-2-one (50 mg, 30%). 1H NMR (CDCl3): 0.81 (m, 2H), 1.07-1.28 (m, 5H), 1.53 (d, 3H), 1.83-1.97 (m, 4H), 2.22 (m, 3H), 2.83 (m, 1H), 3.55 (m, 2H), 5.09 (m, 1H), 5.21 (m, 1H), 5.58 (m, 1H), 6.63-6.77 (m, 2H), 7.04-28 (m, 13H), 7.43 (m, 2H), 7.68 (m, 1H).

Workup

  1. temperatureto reflux overnight
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customto give the crude product, which
  5. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-96013b5f85554f65b110715be83d7043
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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