Aluminium lithium hydride → HCID 11451185, compound

HRID 1985952Notes

Reaction equation

HRID 1985952 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[S:12][C:11]([S:13]([NH:16][CH:17]([CH:22]2[CH2:27][CH:26]3[CH:24]([C:25]3([F:29])[F:28])[CH2:23]2)[C:18](OC)=[O:19])(=[O:15])=[O:14])=[CH:10][CH:9]=1>C1COCC1>[Cl:7][C:8]1[S:12][C:11]([S:13]([NH:16][CH:17]([CH:22]2[CH2:27][CH:26]3[CH:24]([C:25]3([F:29])[F:28])[CH2:23]2)[CH2:18][OH:19])(=[O:14])=[O:15])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 91296289HCID 91296289, compound

Product 1

HCID 11451185HCID 11451185, compoundYield 77.77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a slurry of LAH (0.030 g, 0.78 mmol) in THF (5 mL) was added methyl {[(5-chlorothien-2-yl)sulfonyl]amino}(6,6-difluorobicyclo[3.1.0]hex-3-yl)acetate (0.154 g, 0.38 mmol) dropwise at 0° C. over 20 min. The slurry (gray) was allowed to warm to 25° C. over 19 h. The reaction slurry was cooled to 0° C. and the reaction was quenched with H2O (0.5 mL), 1N NaOH (1.5 mL) and H2O (0.5 mL). The reaction was stirred 4 h to obtain a white slurry. The slurry was filtered and the mother liquor was further dried over MgSO4, filtered, and concentrated in vacuo to obtain a crude yellow oil (0.162 g). The crude product was purified by the Biotage Flash™ 40 chromatography system, eluent: 1:4 EtOAc-hexanes, to afford 5-chloro-N-[1-(6,6-difluorobicyclo[3.1.0]hex-3-yl)-2-hydroxyethyl]thiophene-2-sulfonamide as a colorless oil (0.105 g, 77.77%). Mass Spectrum (−ESI): 356 (M−H)−.

Workup

  1. temperatureThe reaction slurry was cooled to 0° C.
  2. customthe reaction was quenched with H2O (0.5 mL), 1N NaOH (1.5 mL) and H2O (0.5 mL)
  3. customto obtain a white slurry
  4. filtrationThe slurry was filtered
  5. dry with materialthe mother liquor was further dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto obtain a crude yellow oil (0.162 g)
  9. customThe crude product was purified by the Biotage Flash™ 40 chromatography system, eluent

Sources & evidence

ORD record
ord-6605f43dfd25438ab56f5f97863e06e8
Source dataset
uspto-grants-2009_06
Patent number
US07547725B2

Reaction notes

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