Tetrahydrofuran → HCID 68525183, compound

HRID 2246722Notes

Reaction equation

HRID 2246722 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]2([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:7]1=[O:20].C([Li])CCC.[C:29]([SiH:33]([CH3:35])[CH3:34])([CH3:32])([CH3:31])[CH3:30].C1C[O:39][CH2:38][CH2:37]1>>[Si:33]([O:39][CH2:38][CH2:37][CH:5]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]2([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:7]1=[O:20])[C:4]1[CH:21]=[CH:22][CH:23]=[C:2]([F:1])[CH:3]=1)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:35])[CH3:34]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 5072427tert-ButyldimethylsilaneHCID 68526680HCID 68526680, compoundHCID 178418339Butyllithium

Product 1

HCID 68525183HCID 68525183, compoundYield 92%

Conditions

Temperature
0 °C

Procedure

1′-(3-fluorobenzyl)spiro[cyclohexane-1,3′-indol]-2′(1′H)-one (0.61 g, 1.97 mmol) was dissolved in THF and cooled to −78° C. n-Butyl lithium (2.5 M in hexane, 0.87 mL, 2.2 mmol) was added dropwise and the mixture was warmed to 0° C. 2-Bromoethoxy)-tert-butyldimethylsilane (0.65 mL, 3 mmol) was added and the mixture was allowed to warm to 25° C. The mixture was stirred for 16 hours then quenched with saturated aqueous ammonium chloride, diluted with ether, washed with water, and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified via Isco chromatography (Redisep, silica, gradient 0-10% ethyl acetate in hexane) to afford 0.86 g (92%) 1′-[3-{[tert-butyl(dimethyl)silyl]oxy}-1-(3-fluorophenyl)propyl]spiro[cyclohexane-1,3′-indol]-2′(1′H)-one.

Workup

  1. additionwas added dropwise
  2. temperatureto warm to 25° C
  3. customthen quenched with saturated aqueous ammonium chloride
  4. additiondiluted with ether
  5. washwashed with water, and saturated brine
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified via Isco chromatography (Redisep, silica, gradient 0-10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-fb698816ba9d426d8cb875029512f795
Source dataset
uspto-grants-2010_03
Patent number
US07687529B2

Reaction notes

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