Water → HCID 63310725, compound

HRID 2371029Notes

Reaction equation

HRID 2371029 reaction equation
CO[C:3]([C:5]1([NH:8][C:9](=[O:25])[O:10][CH2:11][CH:12]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:7][CH2:6]1)=[O:4].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[CH2:33]1[CH2:37]OC[CH2:34]1>>[OH:4][CH2:3][C:5]1([NH:8][C:9](=[O:25])[O:10][CH2:11][CH:12]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:7][CH2:6][CH2:37][CH2:33][CH2:34]1

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 29921418HCID 29921418, compound

Product 1

HCID 63310725HCID 63310725, compoundYield 90%

Procedure

To a solution of (9H-fluoren-9-yl)methyl 1-(methoxycarbonyl)-cyclopropylcarbamate (15 g, 44.5 mmol) in THF (100 mL) at −5° C. was added LiAlH4 (1.0 g, 26.3 mmol) in portions. After stirring at room temperature for 3 h, water (10 mL) was added to quench the reaction. The mixture was filtered and the filtrate was extracted with EtOAc (3×100 mL). The organic extract was washed with brine, and dried over anhydrous Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the title compound (12.3 g, 90%).

Workup

  1. customto quench
  2. customthe reaction
  3. filtrationThe mixture was filtered
  4. extractionthe filtrate was extracted with EtOAc (3×100 mL)
  5. extractionThe organic extract
  6. washwas washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationAfter filtration and concentration
  9. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-2d598ce98fa7465d8ea87cbd29110618
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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