Tetrahydrofuran → HCID 57803531, compound

HRID 2102998Notes

Reaction equation

HRID 2102998 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[C:13]2[C:8](=[C:9]([CH3:17])[C:10]([CH3:16])=[C:11]([OH:15])[C:12]=2[CH3:14])[S:7][C:6]2([CH2:20][CH2:19][CH2:18]2)[CH2:5]1.C1COCC1.[BH3-]C#N.[Na+]>C(O)(=O)C>[CH3:1][O:2][NH:3][CH:4]1[C:13]2[C:8](=[C:9]([CH3:17])[C:10]([CH3:16])=[C:11]([OH:15])[C:12]=2[CH3:14])[S:7][C:6]2([CH2:20][CH2:19][CH2:18]2)[CH2:5]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 5003444Sodium cyanoborohydrideHCID 73047665HCID 73047665, compound

Product 1

HCID 57803531HCID 57803531, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 6′-hydroxy-5′,7′,8′-trimethylspiro[cyclobutane-1 ,2′-thiochromen]-4′(3′H)-one O-methyloxime, prepared as described above (50 mg) in 2 mL of BH3 1.0 M THF solution was added large excess of NaCNBH3 and 0.5 mL of acetic acid. The reaction mixture was allowed to stir for 5 days. The mixture was washed with water and extracted with ethyl acetate. After concentration in vacuo, the residue was purified by flash chromatography eluted with 20% ethyl acetate in hexane to give 5.4 mg of 4′-(methoxyamino)-5′,7′,8′-trimethyl-3′,4′-dihydrospiro[cyclobutane-1,2′-thiochromen]-6′-ol as a white paste.

Workup

  1. washThe mixture was washed with water
  2. extractionextracted with ethyl acetate
  3. concentrationAfter concentration in vacuo
  4. customthe residue was purified by flash chromatography
  5. washeluted with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-6ca4490cc4f44b02a38875323c941652
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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