Water → HCID 68931295, compound

HRID 1470683Notes

Reaction equation

HRID 1470683 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([C@@H:15]1[C@@H:22]2[C@@H:18]([O:19][C:20](=[O:23])[CH2:21]2)[CH2:17][C@H:16]1[O:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][O:26]1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].O.[OH-].[Na+]>C1COCC1.ClCCl>[OH:23][CH2:20][CH2:21][C@@H:22]1[C@@H:15]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C@H:16]([O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)[CH2:17][C@@H:18]1[OH:19]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68734777HCID 68734777, compound

Product 1

HCID 68931295HCID 68931295, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiAlH4 (1.5 mL, 1.5 mmol, 1 M/THF) was added to a 0° C. solution of 5-4 (453 mg, 1.34 mmol) in THF (5 mL). After 3 h, H2O (5 mL) was added dropwise followed by dichloromethane and 15% NaOH (10 mL). The reaction was allowed to warm to room temperature and was stirred further for 30 min. The resulting mixture was extracted with dichloromethane (3×) and the combined dichloromethane solution was dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography on silica gel (Isco Combiflash unit) gave the title compound (447 mg, 97%).

Workup

  1. extractionThe resulting mixture was extracted with dichloromethane (3×)
  2. dry with materialthe combined dichloromethane solution was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification of the residue by flash chromatography on silica gel (Isco Combiflash unit)

Sources & evidence

ORD record
ord-90ad297966f044e3b1d87590c173062c
Source dataset
uspto-grants-2015_04
Patent number
US09006464B2

Reaction notes

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