Phthalic Anhydride → HCID 86687009, compound

HRID 1402145Notes

Reaction equation

HRID 1402145 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-fe9ec65e536d4722b96ad7e36f83c8f8
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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