Dimethyl Sulfide → HCID 10471109, compound

HRID 1651416Notes

Reaction equation

HRID 1651416 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C@@H:8]([NH:12][C:13](=O)[C@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=3)[OH:15])[CH2:9]2)=[CH:4][CH:3]=1.B.CSC.B#B.B.CSC>O1CCCC1.CO>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C@@H:8]([NH:12][CH2:13][C@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=3)[OH:15])[CH2:9]2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 1068Dimethyl SulfideHCID 6331BoraneHCID 6328200DiboronHCID 10382056HCID 10382056, compoundHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 10471109HCID 10471109, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3 g of N-[(2R)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]-(S)-3-chloromandelamide, SR 58588, PREPARATION VI, in 40 ml of anhydrous tetrahydrofuran, heated with reflux under nitrogen stream, there is added 2.7 ml of a 10M solution of borane-methylsulfide (reagent which generates diborane consisting of a complex of borane and dimethylsulfide) in 20 ml of tetrahydrofuran, and heated for 4 hours with reflux. To the solution cooled at room temperature, there is added 25 ml of methanol and the reaction mixture is left under stirring at first 30 minutes at room temperature, then, 30 minutes with reflux. After concentration under reduced pressure and filtration, the residue is crystallized twice from isopropanol to give the N-[(2R)-7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl]-(2S)-2-(3-chlorophenyl)-2-hydroxyethanamine, SR 58590; m.p. 186°-188° C.; |alpha|=+76° (methanol, c=0.5%).

Workup

  1. temperaturewith reflux under nitrogen stream, there
  2. temperatureheated for 4 hours
  3. temperaturewith reflux
  4. waitthe reaction mixture is left
  5. temperature30 minutes with reflux
  6. concentrationAfter concentration
  7. filtrationunder reduced pressure and filtration
  8. customthe residue is crystallized twice from isopropanol

Sources & evidence

ORD record
ord-737720b3c01b435ca917a9fa6c9e06d2
Source dataset
uspto-grants-1990_05
Patent number
US04927955

Reaction notes

Loading…