Sodium Bicarbonate → HCID 86605480, compound

HRID 2103024Notes

Reaction equation

[OH:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:12](=[CH:13][C:14]=1[CH3:15])[O:11][C:7]1([CH2:10][CH2:9][CH2:8]1)[CH2:6][C:5]2=[N:16][OH:17].Cl.O1CCOCC1.C([O-])(O)=O.[Na+]>C1COCC1>[OH:17][NH:16][CH:5]1[C:4]2[C:12](=[CH:13][C:14]([CH3:15])=[C:2]([OH:1])[C:3]=2[CH3:18])[O:11][C:7]2([CH2:10][CH2:9][CH2:8]2)[CH2:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

1.0 g of 6-hydroxy-5,7-dimethylspiro[chromene-2,1′-cyclobutan]-4(3H)-one oxime was dissolved in 20 mL of THF and cooled to 0° C. under nitrogen. 3 mL of (8M) borane-pyridine complex was added via syringe followed by 12 mL of (4 M) HCl-dioxane via a syringe pump over 45 min. After complete addition, the ice bath was removed and the reaction slowly warmed to room temperature then stirred overnight. The next day, the solution was added to sat. NaHCO3, extracted with EtOAc, washed with additional sat. NaHCO3, brine and dried over Na2SO4. The crude material was purified on a silica column eluting with 1:8 EtOAc/Hexanes to yield 699 mg of 4-(hydroxyamino)-5,7-dimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-ol.

Workup

addition3 mL of (8M) borane-pyridine complex was added via syringe
additionAfter complete addition
customthe ice bath was removed
customthe reaction
temperatureslowly warmed to room temperature
extractionextracted with EtOAc
washwashed with additional sat. NaHCO3, brine
dry with materialdried over Na2SO4
customThe crude material was purified on a silica column
washeluting with 1:8 EtOAc/Hexanes

Sources & evidence

ORD record: ord-310eee5ebc0646d0958e8cc0591a0fad
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576094B2

Reaction notes

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