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

HRID 1984766Notes

Reaction equation

HRID 1984766 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>[OH:12][CH:9]1[CH2:10][C:11]2[C:2]([NH:1][C:20](=[O:21])[O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:3][CH:4]=[CH:5][C:6]=2[CH2:7][CH2:8]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 ethylacetate. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The obtained residue was triturated with ethylacetate and hexane to afford phenyl (7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)carbamate (25.2 mg, 48% yield).

Workup

  1. extractionextracted with ethylacetate
  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 ethylacetate and hexane

Sources & evidence

ORD record
ord-28283cbb54594510ac6785fdf3a3b007
Source dataset
uspto-grants-2009_06
Patent number
US07544716B2

Reaction notes

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