Tetrahydrofuran → HCID 57847038, compound

HRID 550301Notes

Reaction equation

HRID 550301 reaction equation
[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].O1CCCC1.[O:11]=[C:12]([NH:21][C@@H:22]1[CH2:27][CH2:26][CH2:25][CH2:24][C@@H:23]1[C:28]([N:30]1[C@@H:42]2[C@@H:33]([C@H:34]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[NH:35][C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][C:41]=32)[CH2:32][CH2:31]1)=[O:29])[CH2:13][CH2:14][CH2:15][CH2:16][C:17](OC)=[O:18]>O.C(O)C>[OH:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]([NH:21][C@@H:22]1[CH2:27][CH2:26][CH2:25][CH2:24][C@@H:23]1[C:28]([N:30]1[C@@H:42]2[C@@H:33]([C@H:34]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[NH:35][C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][C:41]=32)[CH2:32][CH2:31]1)=[O:29])=[O:11]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 57847323HCID 57847323, compound

Product 1

HCID 57847038HCID 57847038, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of calcium chloride (88 mg, 0.8 mmol), sodium borohydride (60 mg, 1.6 mmol), tetrahydrofuran (2.5 ml) and ethanol (2.5 ml) was stirred under a nitrogen atmosphere under ice-cooling for 30 min. To the mixture was added methyl 6-oxo-6-[((1R,2S)-2-{[(3aR,4R,9bR)-4-phenyl-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexyl)amino]hexanoate (106 mg, 0.20 mmol) under ice-cooling, and the mixture was stirred at room temperature for 16 hrs. Water was added, and the reaction mixture was extracted with ethyl acetate. The extract was dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to column chromatography using basic silica gel and eluted with ethyl acetate to give the title compound (89 mg, 92%) as a white solid.

Workup

  1. temperaturecooling for 30 min
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 16 hrs
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous Na2SO4
  6. customThe solvent was evaporated under reduced pressure
  7. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-2a5d7cfd44c840769930729a11749c05
Source dataset
uspto-grants-2011_05
Patent number
US07943770B2

Reaction notes

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