Sodium cyanoborohydride → HCID 11708700, compound

HRID 2103006Notes

Reaction equation

HRID 2103006 reaction equation
[OH:1][C:2]1[C:3]([CH3:20])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][CH:7]([CH:14]1[CH2:17][CH2:16]C1)[C:6]([CH:18]=[O:19])=[CH:5]2.[BH3-]C#N.[Na+]>C1COCC1.CC(O)=O>[OH:19][CH2:18][C:6]1[C:7]2([CH2:16][CH2:17][CH2:14]2)[O:8][C:9]2[C:4](=[C:3]([CH3:20])[C:2]([OH:1])=[C:11]([CH3:12])[C:10]=2[CH3:13])[CH:5]=1

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 86605477HCID 86605477, compound

Product 1

HCID 11708700HCID 11708700, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6-hydroxy-5,7,8-trimethyl-2-cyclobutyl-chromene-3-carbaldehyde (250 mg) in 10 mL of THF and 1 mL of AcOH was added NaCNBH3 (305 mg). The reaction mixture was allowed to stir at room temperature for 6 h. The mixture was concentrated and the residue was purified by flash chromatography eluted with 30% ethyl acetate in hexane to give 135 mg of 3-(hydroxymethyl)-5,7,8-trimethylspiro[chromene-2,1′-cyclobutan]-6-ol as a light yellow solid. 1H-NMR (300 MHz, MeOD) δ=6.52 (s, 1H, C═CH), 4.35 (s, 1H), 2.36 (m, 4H), 2.20-1.75 (m, 11H) ppm. 13C-NMR (75 MHz, MeOD) δ=146.5, 144.5, 137.6, 124.9, 122.2, 119.3, 118.4, 117.0, 80.7, 62.0, 32.7, 14.3, 12.2, 11.2, 10.7 ppm. MS:(m/z)=243.2 (M−18+), 283.1 (M+Na+).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by flash chromatography
  3. washeluted with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d9ff24c3f1a44252ab3ff45893ee5b34
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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