Water → (1S)-1-(4-benzyloxy-phenyl)-2-[((2S)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)amino]ethanol

HRID 1003284Notes

Reaction equation

HRID 1003284 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]([OH:30])[C:16]([NH:18][C@H:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][C:23]([OH:29])=[CH:24][CH:25]=3)[CH2:20]2)=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N(CCO)(CCO)CCO.O>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@H:15]([OH:30])[CH2:16][NH:18][C@H:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][C:23]([OH:29])=[CH:24][CH:25]=3)[CH2:20]2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7618TriethanolamineHCID 57222877(2S)-2-(4-Benzyloxyphenyl)-2-hydroxy-N-((2S)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide

Product 1

HCID 57111737(1S)-1-(4-benzyloxy-phenyl)-2-[((2S)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)amino]ethanolYield 67.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(2S)-2-(4-Benzyloxyphenyl)-2-hydroxy-N-((2S)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide (2.50 g) was dissolved in tetrahydrofuran (31 ml), and borane-dimethyl-sulfide complex (1.76 ml) was added to the solution. After the mixture was heated under reflux for 4 hours, a solution of triethanolamine (4.62 g) in tetrahydrofuran (4.6 ml) was added to the reaction mixture and the mixture was heated under reflux for 11 hours. After cooling, water was poured into the reaction mixture and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. Purification of the residue by medium pressure liquid column chromatography on silica gel (eluent: ethyl acetate/ethanol=7/1) gave (1S)-1-(4-benzyloxy-phenyl)-2-[((2S)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)amino]ethanol (1.63 g) as an amorphous.

Workup

  1. additionborane-dimethyl-sulfide complex (1.76 ml) was added to the solution
  2. temperatureAfter the mixture was heated
  3. temperatureunder reflux for 4 hours
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 11 hours
  6. temperatureAfter cooling
  7. extractionthe resulting mixture was extracted with ethyl acetate
  8. washThe extract was washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was removed in vacuo
  11. customPurification of the residue by medium pressure liquid column chromatography on silica gel (eluent: ethyl acetate/ethanol=7/1)

Sources & evidence

ORD record
ord-73a21adc88114ae2b962c8df734f0663
Source dataset
uspto-grants-2000_04
Patent number
US06046192

Reaction notes

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