Diethyl Ether → HCID 86748409, compound

HRID 1769647Notes

Reaction equation

HRID 1769647 reaction equation
[CH2:1]([NH:4][C@H:5]1[CH2:14][CH2:13][C:12]2[C:11]([OH:15])=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6]1)[CH2:2][CH3:3].C(=O)(O)[O-].[Na+].Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].CCOCC>O>[OH:15][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[CH2:13][CH2:14][C@H:5]([N:4]([CH2:1][CH2:2][CH3:3])[C:22](=[O:23])[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:6]2

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 10219902(6S)-6-(Propylamino)-5,6,7,8-tetrahydronaphthalen-1-ol

Product 1

HCID 86748409HCID 86748409, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirring suspension of (S)-6-propylamino-5,6,7,8-tetrahydro-l-naphthalenol (7.34 g, 0.0257 mol) in water (100 mL) was cooled in an ice bath and sodium bicarbonate (8.49 g, 0,101 mol) was added. This suspension was stirred for fifteen minutes then benzyl chloroformate (4.50 g, 0.0264 mol) was added dropwise. The mixture was stirred for fifteen minutes and then allowed to come to room temperature. Ether (100 mL) was added and the mixture was stirred overnight. The layers were separated and the aqueous layer was extracted with ether. The combined organic layers were washed twice with saturated aqueous sodium bicarbonate, once with water, twice with dilute hydrochloric acid, once with water and once with saturated aqueous sodium chloride, dried (magnesium sulfate) and concentrated under reduced pressure to give 7.09 g (81% yield) of product as a yellow solid.

Workup

  1. temperaturewas cooled in an ice bath
  2. stirringThe mixture was stirred for fifteen minutes
  3. customto come to room temperature
  4. stirringthe mixture was stirred overnight
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with ether
  7. washThe combined organic layers were washed twice with saturated aqueous sodium bicarbonate, once with water, twice with dilute hydrochloric acid, once with water and once with saturated aqueous sodium chloride
  8. dry with materialdried (magnesium sulfate)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-55cfc5a86d324534b531e1ad06d969f2
Source dataset
uspto-grants-1995_01
Patent number
US05382596

Reaction notes

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