Methanol → HCID 10471109, compound

HRID 1614755Notes

Reaction equation

HRID 1614755 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.CO>O1CCCC1>[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

4

Reactant 2

HCID 887MethanolHCID 10382056HCID 10382056, compound

Product 1

HCID 10471109HCID 10471109, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 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, described in Example 8(b), in 40 ml of anhydrous tetrahydrofuran, heated with reflux under nitrogen stream, there is added 2.7 ml of a 10M solution of boranemethylsulfide in 20 ml of tetrahydrofuran, and the refluxing is maintained for 4 hours. To the solution cooled to room temperature, there is added 25 ml of methanol and the reaction mixture is left under stirring at first at room temperature for 30 minutes and then at reflux for 30 minutes. The solution is concentrated under reduced pressure and, after filtration, the product is crystallized twice from isopropanol. There is obtained 2.1 g (73%) of 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. temperatureheated
  2. temperaturewith reflux under nitrogen stream, there
  3. temperaturethe refluxing is maintained for 4 hours
  4. waitthe reaction mixture is left
  5. temperatureat reflux for 30 minutes
  6. concentrationThe solution is concentrated under reduced pressure
  7. filtrationafter filtration
  8. customthe product is crystallized twice from isopropanol

Sources & evidence

ORD record
ord-0e2aa30e359a45719a8c5adfdd300c32
Source dataset
uspto-grants-1993_03
Patent number
US05198586

Reaction notes

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