Pyridine → HCID 69012857, compound

HRID 1432832Notes

Reaction equation

HRID 1432832 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][C@H: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].C(OC(=O)C)C>C1COCC1>[C:23]1([O:22][C:20](=[O:21])[NH:1][C:2]2[C:11]3[CH2:10][C@H: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 1049PyridineHCID 8857Ethyl AcetateHCID 15891Phenyl chloroformateHCID 57936087(2R)-8-Amino-1,2,3,4-tetrahydro-2-naphthalenol

Product 1

HCID 69012857HCID 69012857, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Next, a solution of (R)-8-amino-1,2,3,4-tetrahydro-naphthalen-2-ol -(36.2 g) and pyridine (18.8 ml) in THF (850 ml) cooled at 0° C. was added phenyl chloroformate (28.8 ml). The mixture was stirred for 3 hours at room temperature, and then poured into ethylacetate. The mixture was washed with aqueous NH4Cl then with water, and the organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. To the obtained residue was added acetonitrile, and the precipitates were collected and washed with a mixture of acetonitrile and diisopropyl ether (2:3) to obtain {(R)-7-Hydroxy-5,6,7,8-tetrahydro-naphthalen-1-yl}carbamic acid phenyl ester (33.0 g).

Workup

  1. washThe mixture was washed with aqueous NH4Cl
  2. dry with materialwith water, and the organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. additionTo the obtained residue was added acetonitrile
  6. customthe precipitates were collected
  7. washwashed with a mixture of acetonitrile and diisopropyl ether (2:3)

Sources & evidence

ORD record
ord-1bc980a22fb04358a71adfa1d1c64175
Source dataset
uspto-grants-2009_11
Patent number
US07612113B2

Reaction notes

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