Tetrahydrofuran → HCID 57803521, compound

HRID 2103009Notes

Reaction equation

HRID 2103009 reaction equation
C([O:4][C:5]1[C:6]([CH3:21])=[C:7]2[C:15](=[C:16]([CH3:19])[C:17]=1[CH3:18])[O:14][C:10]1([CH2:13][CH2:12][CH2:11]1)[CH2:9][C:8]2=[O:20])(=O)C.C[Si]([C:26]#[N:27])(C)C.C1COCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOC(C)=O>[NH2:27][CH2:26][C:8]1([OH:20])[C:7]2[C:15](=[C:16]([CH3:19])[C:17]([CH3:18])=[C:5]([OH:4])[C:6]=2[CH3:21])[O:14][C:10]2([CH2:11][CH2:12][CH2:13]2)[CH2:9]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 82115Trimethylsilyl cyanideHCID 21226445Aluminium lithium hydrideHCID 69055283HCID 69055283, compound

Product 1

HCID 57803521HCID 57803521, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 5,7,8-trimethyl-4-oxo-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-yl acetate (2 g), Znl2 (100 mg) and trimethylsilyl cyanide (4 mL) was stirred at 70° C. for 2 h. A homogeneous solution was obtained. The solution was cooled down to room temperature, and THF (30 mL) was added, followed by 1 g of lithium aluminum hydride. After stirring at 60° C. for 3 h, the solution was cooled down and EtOAc was added to destroy excess lithium aluminum hydride. The mixture was poured into water and extracted with EtOAc. The EtOAc was washed with water and dried. After evaporation a white solid was obtained (1 g), which was washed with DCM to give 4-(aminomethyl)-5,7,8-trimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutane]-4,6-diol. 1H-NMR (300 MHz, CDCl3+CD3OD): δ=2.85 (AB, J=13.44 Hz, 2H), 2.36 (s, 2H), 2.35-1.60 (m, 6H), 2.11 (s, 9H) ppm. 13C-NMR (75 MHz, CDCl3+CD3OD) δ=146.82, 145.54, 124.91, 123.75, 121.01, 120.48, 76.49, 75.64, 50.07, 44.97, 34.46, 32.36, 13.75, 13.31, 12.50, 12.22 ppm. MS: (m/z)=260 (M+−OH).

Workup

  1. customA homogeneous solution was obtained
  2. temperatureThe solution was cooled down to room temperature
  3. stirringAfter stirring at 60° C. for 3 h
  4. temperaturethe solution was cooled down
  5. customto destroy excess lithium aluminum hydride
  6. additionThe mixture was poured into water
  7. extractionextracted with EtOAc
  8. washThe EtOAc was washed with water
  9. customdried
  10. customAfter evaporation a white solid
  11. customwas obtained (1 g), which
  12. washwas washed with DCM

Sources & evidence

ORD record
ord-f9dff6f7e74b421f8b1a1951f05263b4
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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