Hydrochloric Acid → HCID 58909230, compound

HRID 1991510Notes

Reaction equation

HRID 1991510 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[O:11][CH2:10][CH2:9][C@@H:8]2[NH:15]C(=O)OC(C)(C)C)([CH3:3])[CH3:2].Cl>CO>[CH:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[O:11][CH2:10][CH2:9][C@@H:8]2[NH2:15])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 60206842HCID 60206842, compound

Product 1

HCID 58909230HCID 58909230, compoundYield 104.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (4S)-6-isopropoxy-3,4-dihydro-2H-chromen-4-ylcarbamate (340 mg, 1.11 mmol) in methanol (2 mL) was added hydrochloric acid (2 mL, 4 N in 1,4-dioxane, 8 mmol). The reaction mixture was stirred at room temperature for 2 h. The solvent was removed under reduced pressure. The residue was diluted with methylene chloride (50 mL) and water (50 mL). The organic layer was separated and the aqueous layer was extracted with methylene chloride (2×50 mL). The combined extracts were washed with saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide (4S)-6-isopropoxychroman-4-amine (240 mg, 99% crude yield): 1H NMR (300 MHz, CDCl3) δ 6.96 (d, J=2.7 Hz, 1H), 6.90-6.86 (m, 1H), 6.80 (d, J=9.0 Hz, 1H), 4.55-4.46 (m, 2H), 4.24-4.17 (m, 2H), 2.40-2.31 (m, 1H), 2.18-2.08 (m, 1H), 1.28 (d, J=6.0 Hz, 6H). This material was used in the next step without further purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with methylene chloride (50 mL) and water (50 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with methylene chloride (2×50 mL)
  5. washThe combined extracts were washed with saturated sodium chloride
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8b3746579465496d82ad7855031edead
Source dataset
uspto-grants-2010_01
Patent number
US07645780B2

Reaction notes

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