Water → HCID 22033409, compound

HRID 1792326Notes

Reaction equation

HRID 1792326 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][C:18]1(O)[C:27]2[C:22](=[CH:23][C:24]([O:28][CH3:29])=[CH:25][CH:26]=2)[S:21][CH2:20][C:19]1([C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=1)[CH3:30])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([BH3-])#N.[Na+].O.CCCCCC>ClCCCl.C(OCC)(=O)C>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][CH:18]1[C:27]2[C:22](=[CH:23][C:24]([O:28][CH3:29])=[CH:25][CH:26]=2)[S:21][CH2:20][C:19]1([C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=1)[CH3:30])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 5003444Sodium cyanoborohydrideHCID 22033274HCID 22033274, compound

Product 1

HCID 22033409HCID 22033409, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-[9-(t-butyldimethylsilyloxy)-1-nonynyl]-3-(4-fluorophenyl)-4-hydroxy-7-methoxy-3-methylthiochroman (0.55 g, 0.99 mmol) in 1,2-dichloroethane (30 ml) were added zinc iodide(II) (0.35 g) and sodium cyanoborohydride (0.30 g), which was then stirred at 0° C. for 4 hours. After the reaction was completed, water was poured thereto, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a crude product. This crude product was subjected to silica gel column chromatography (n-hexane:ethyl acetate=10:1) to give 4-[9-(t-butyldimethylsilyloxy)-1-nonynyl]-3-(4-fluorophenyl)-7-methoxy-3-methylthiochroman (374 mg, yield 70%). This product thus obtained (374 mg) was dissolved in a solvent mixture of ethanol (30 ml) and tetrahydrofuran (10 ml), 20% palladium hydroxide carbon (0.16 g) washed with the reaction solvent was added, and the mixture was stirred under hydrogen at room temperature for 20 hours. The reaction solution was filtered through a cellite to remove the palladium carbon, and the filtrate was concentrated under reduced pressure to give the crude product. This crude product thus obtained was subjected to silica gel column chromatography (n-hexane:ethyl acetate-5:1) to give 4-(9-hydroxynonyl)-3-(4-fluorophenyl)-7-methoxy-3-methylthiochroman (a mixture of (3RS,4RS) and (3RS,4SR), (3RS,4RS)/(3RS,4SR)=about 6/1) (220 mg, yield 74%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a crude product

Sources & evidence

ORD record
ord-5143708b47c74390a9face0dd7321d0a
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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