Water → HCID 54072388, compound

HRID 367345Notes

Reaction equation

HRID 367345 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][C:10]=1[CH2:31][CH2:32][O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=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:14]=[CH:13][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:11][C:10]=1[CH2:31][CH2:32][O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7618TriethanolamineHCID 53900526HCID 53900526, compound

Product 1

HCID 54072388HCID 54072388, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(-)-(2R)-2-[4-Benzyloxy-3-(2-benzyloxyethyl)phenyl]-2-hydroxy-N-((2S)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide (low polarity isomer) (1.08 g) was dissolved in 20 ml of tetrahydrofuran, 438 μl of borane-dimethylsulfide complex was added to the solution, and the mixture was heated under reflux for 3 hours. Then, a solution of 1.14 g of triethanolamine in 1 ml of tetrahydrofuran was added and the mixture was again heated under reflux for 6 hours. After cooling, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and then dried over anhydrous magnesium sulfate. Thereafter, the solvent was evaporated under reduced pressure and the resulting residue was recrystallized from ethyl acetate to give 687 mg of (-)-(1R)-1-[4-benzyloxy-3-(2-benzyloxyethyl)phenyl]-2-((2S)-7-hydroxy-1,2,3,4-tetrahydronaphthalen-2-ylamino)ethanol having a melting point of 147 to 150° C.

Workup

  1. addition438 μl of borane-dimethylsulfide complex was added to the solution
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 3 hours
  4. temperaturethe mixture was again heated
  5. temperatureunder reflux for 6 hours
  6. temperatureAfter cooling
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe extract was washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThereafter, the solvent was evaporated under reduced pressure
  11. customthe resulting residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-59a671e7510f431280976aba635f5153
Source dataset
uspto-grants-2000_10
Patent number
US06133266

Reaction notes

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