Phthalic Anhydride → HCID 86687009, compound

HRID 2282421Notes

Reaction equation

HRID 2282421 reaction equation
[NH2:1][C@@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@H:5]([OH:12])[CH2:4][CH2:3]1.[C:13]1(=O)[O:18][C:16](=[O:17])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12>C1(C)C=CC=CC=1>[OH:12][C@H:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C@@H:2]([N:1]2[C:16](=[O:17])[C:15]3[C:14](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:13]2=[O:18])[CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 86686674(1R,4S)-4-Amino-1,2,3,4-tetrahydronaphthalen-1-ol

Product 1

HCID 86687009HCID 86687009, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of Intermediate A (150 mg, 0.92 mmol) and phthalic anhydride (143 mg, 0.97 mmol) in toluene (9 mL) was stirred and heated at reflux for 19.5 h. After cooling, the mixture was concentrated in vacuo. The residue was purified by FCC, using 0-50% EtOAc in cyclohexane, to give the title compound as white powder (215 mg, 79%). LCMS (Method 3): Rt 3.36 min, m/z 316 [MNa+].

Workup

  1. temperatureheated
  2. temperatureat reflux for 19.5 h
  3. temperatureAfter cooling
  4. concentrationthe mixture was concentrated in vacuo
  5. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-ef2c0ccb2f4d409bbb2ac62d48710390
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

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