Water → Phenyl (7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)carbamate

HRID 30534Notes

Reaction equation

HRID 30534 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]2.N1C=CC=CC=1.Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21].O>C1COCC1>[C:23]1([O:22][C:20](=[O:21])[NH:1][C:2]2[C:11]3[CH2:10][CH:9]([OH:12])[CH2:8][CH2:7][C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 15891Phenyl chloroformateHCID 230669958-Amino-1,2,3,4-tetrahydronaphthalen-2-ol

Product 1

HCID 59731048Phenyl (7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)carbamateYield 49.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 8-amino-1,2,3,4-tetrahydro-naphthalen-2-ol (30.0 mg, 0.18 mmol) and pyridine (21.8 mg, 0.28 mmol) in 1.0 mL THF was added phenyl chloroformate (30.2 mg, 0.19 mmol), and the mixture was stirred for 1 hour at room temperature. To the product mixture was added water and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The obtained residue was triturated with ethyl acetate and hexane to afford (7-hydroxy-5,6,7,8-tetrahydro-naphthalen-1-yl)carbamic acid phenyl ester (25.2 mg, 48% yield).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was triturated with ethyl acetate and hexane

Sources & evidence

ORD record
ord-06a448c7666b4b8c85d82ad5ffbbd9c8
Source dataset
uspto-grants-2008_09
Patent number
US07423175B2

Reaction notes

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