Water → (S)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamic acid ethyl ester

HRID 606292

Reaction equation

HRID 606292 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[C@@H:7]1([NH2:17])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][CH2:8]1.C([O-])([O-])=O.[K+].[K+].O>CC#N>[CH2:5]([O:4][C:2](=[O:3])[NH:17][C@@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][CH2:8]1)[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 70580741-Aminotetralin, (S)-

Product 1

HCID 7768470(S)-(1,2,3,4-tetrahydro-naphthalen-1-yl)carbamic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl chloroformate (7.74 g, 71.3 mmol) is added dropwise to a mixture of (S)-1,2,3,4-tetrahydro-naphthalen-1-ylamine (10.0 g, 67.9 mmol) and K2CO3 (18.8 g, 136 mmol) in CH3CN (100 mL). The resulting mixture is stirred at room temperature overnight. Water (100 mL) is added and the mixture is extracted with ether (2×100 mL). The combined extract is washed with 1 N HCl (2×10 mL), water, dried (Na2SO4), and concentrated in vacuo to give (S)-(1,2,3,4-tetrahydro-naphthalen-1-yl)-carbamic acid ethyl ester as a solid.

Workup

  1. extractionthe mixture is extracted with ether (2×100 mL)
  2. extractionThe combined extract
  3. washis washed with 1 N HCl (2×10 mL), water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-db36890a6eb64c089fc51b20a96349ca
Source dataset
uspto-grants-2011_03
Patent number
US07915288B2

Linked notes

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