Hydrochloric Acid → 2-((1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl)acetic acid

HRID 2056720Notes

Reaction equation

HRID 2056720 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:10]([CH2:11][C:12]([OH:14])=[O:13])[O:9][CH2:8][CH2:7][C:6]=2[CH:15]=1.CC1C=CC([C@H](N)C)=CC=1.Cl>C(#N)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C@H:10]([CH2:11][C:12]([OH:14])=[O:13])[O:9][CH2:8][CH2:7][C:6]=2[CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7015756(+)-1-(4-Methylphenyl)ethylamineHCID 10540012(6-Bromoisochroman-1-yl)acetic acid

Product 1

HCID 106357992-((1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×

Procedure

To a suspension of 2-(6-bromo-3,4-dihydro-1H-2-benzopyran-1-yl)acetic acid (55 g, 203 mmol) in acetonitrile (375 mL) and water (40 mL) was added a solution of (R)-1-(4-methylphenyl)ethylamine (27.45 g, 203 mmol) in acetonitrile (370 mL). The mixture was heated to reflux and the resulting solution cooled to room temperature. A precipitate appeared upon cooling. After stirring for 2 h the salt was filtered off, washed with 95/5 acetonitrile/water (80 mL), and dried in vacuo. The salt was recrystallized in 95/5 acetonitrile/water to give a solid which was suspended in water (390 mL) and treated with 6N HCl (17 mL). After stirring for 1.5 h, filtration, washing, and drying gave the title compound (98% e.e.) as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureupon cooling
  4. filtrationwas filtered off
  5. washwashed with 95/5 acetonitrile/water (80 mL)
  6. customdried in vacuo
  7. customThe salt was recrystallized in 95/5 acetonitrile/water
  8. customto give a solid which
  9. stirringAfter stirring for 1.5 h
  10. filtrationfiltration
  11. washwashing
  12. customdrying

Sources & evidence

ORD record
ord-8be113703030499d85c36797b9841b5e
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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