(1S,2S)-(+)-N-p-Tosyl-1,2-diphenylethylenediamine → (S)-6,8-Dibromochroman-4-ol

HRID 1008958Notes

Reaction equation

HRID 1008958 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Br:12])[CH:11]=1)[O:8][CH2:7][CH2:6][C:5]2=[O:13].C(O)=O.C(N(CC)CC)C.CC1C=CC(S(N[C@H]([C@@H](N)C2C=CC=CC=2)C2C=CC=CC=2)(=O)=O)=CC=1>C(#N)C.C(OC(=O)C)C.CC1C=CC(C(C)C)=CC=1.CC1C=CC(C(C)C)=CC=1.Cl[Ru]Cl.Cl[Ru]Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Br:12])[CH:11]=1)[O:8][CH2:7][CH2:6][C@@H:5]2[OH:13]

Participants

7

Reactant 3

HCID 6612782(1S,2S)-(+)-N-p-Tosyl-1,2-diphenylethylenediamineHCID 11084032Triethylammonium formateHCID 534011896,8-Dibromochroman-4-one

Product 1

HCID 67304261(S)-6,8-Dibromochroman-4-ol

Reagents, catalysts & solvents 3

HCID 10908223Dichloro(p-cymene)ruthenium(II) dimerCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture containing 6,8-dibromochroman-4-one in acetonitrile (0.3M) and 5/2 formic acid/triethylamine (30% by volume) was added (1S,2S)-(+)-N-p-tosyl-1,2-diphenylethylene diamine (1 mol %) and dichloro(p-cymene)-ruthenium (II) dimer (0.5 mol %). After stirring for 24 h, the reaction was diluted with ethylacetate and washed with brine/sodium bicarbonate (1:1). The organic phase was concentrated under reduced pressure to afford the title compound as a tan solid.

Workup

  1. washwashed with brine/sodium bicarbonate (1:1)
  2. concentrationThe organic phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0ee4c634c6064be5b65f8e63bccbe2f0
Source dataset
uspto-grants-2011_07
Patent number
US07973050B2

Reaction notes

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