Phthalic Anhydride → HCID 66618179, compound

HRID 222200Notes

Reaction equation

HRID 222200 reaction equation
[NH2:1][C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@H:3]1[OH:11].[C:12]1(=O)[O:17][C:15](=[O:16])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.C(N(CC)C(C)C)(C)C>C1(C)C=CC=CC=1>[OH:11][C@@H:3]1[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C@H:2]1[N:1]1[C:15](=[O:16])[C:14]2[C:13](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]1=[O:17]

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 81531DiisopropylethylamineHCID 69311541-Amino-2-indanol, trans-(-)-

Product 1

HCID 66618179HCID 66618179, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of (1R,2R)-1-aminoindan-2-ol (1.40 g, 0.00938 mol), phthalic anhydride (1.39 g, 0.00938 mol), and N,N-diisopropylethylamine (1.63 mL, 0.00935 mol) in toluene (141 mL) in a 250 mL round bottom flask equipped with a Dean-Stark trap and condenser was stirred at reflux under an atmosphere of nitrogen 18 h. The reaction mixture was cooled to rt. TLC showed complete conversion of starting material to a higher Rf spot. 1H NMR of an aliquot sample partitioned between EtOAc and water confirmed that reaction was complete. The reaction mixture was concentrated to a pale white and pale brown solid, redissolved in EtOAc (25 mL), washed with 1N HCl (2×10 mL), aqueous saturated NaHCO3 (1×10 mL), and brine (1×10 mL), dried over Na2SO4, filtered, concentrated, and dried on high vacuum to give the product as an off-white solid (2.53 g, 97%). 1H NMR (CDCl3, 400 MHz, δ): 7.86-7.84 (m, 2H), 7.74-7.72 (m, 2H), 7.26-7.25 (m, 2H), 7.20-7.14 (m, 1H), 7.01 (d, J=7.5 Hz, 1H), 5.67 (d, J=6.3 Hz, 1H), 5.14 (m, 1H), 3.58 (dd, J=7.5, 16.1 Hz, 1H), 2.97 (dd, J=6.8, 15.8 Hz, 1H), 2.12 (s, 1H) ppm.

Workup

  1. customequipped with a Dean-Stark trap and condenser
  2. temperatureat reflux under an atmosphere of nitrogen 18 h
  3. custom1H NMR of an aliquot sample partitioned between EtOAc and water
  4. customconfirmed that reaction
  5. concentrationThe reaction mixture was concentrated to a pale white and pale brown solid
  6. dissolutionredissolved in EtOAc (25 mL)
  7. washwashed with 1N HCl (2×10 mL), aqueous saturated NaHCO3 (1×10 mL), and brine (1×10 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customdried on high vacuum

Sources & evidence

ORD record
ord-844d4fef25944e70945965e337c32cb8
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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