Tetrahydrofuran → HCID 9936868, compound

HRID 380512Notes

Reaction equation

HRID 380512 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[C:17]([N:19]2[CH2:23][C@@H:22]([C:24]3[CH:28]=[CH:27][S:26][CH:25]=3)[C@H:21]([CH2:29][N:30]3[CH2:35][CH2:34][CH:33]([C:36]4[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=4)[CH2:32][CH2:31]3)[CH2:20]2)=[O:18])[CH:10]=[C:9]1C)=O)(C)(C)C.[Li+].[BH4-].C([O-])(O)=O.[Na+].[OH-].[Na+].C1C[O:56][CH2:55][CH2:54]1>CCOCC>[OH:56][CH2:55][CH2:54][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[C:17]([N:19]2[CH2:23][C@@H:22]([C:24]3[CH:28]=[CH:27][S:26][CH:25]=3)[C@H:21]([CH2:29][N:30]3[CH2:31][CH2:32][CH:33]([C:36]4[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=4)[CH2:34][CH2:35]3)[CH2:20]2)=[O:18])[CH:10]=[CH:9]1

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 86757489HCID 86757489, compound

Product 1

HCID 9936868HCID 9936868, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 0.07 g (0.115 mmol) of 1-(1-t-butoxycarbonyl methyl-7-indolecarbonyl)-3-(R)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(R)-(3-thienyl)pyrrolidine and 0.23 mL (0.46 mmol) of LiBH4 (2M in THF) in 4 mL of THF was stirred at rt for 12 h. To the reaction mixture was slowly added 2 mL of sat. NaHCO3 solution and the mixture was stirred st rt for 3 h. To this mixture was then added 30 mL of ether and the pH was adjusted to pH=10-11 with 5N NaOH solution. The reaction mixture was extracted with CH2Cl2. The organic fraction was dried over Na2CO3, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, CH2Cl2: ethyl acetate: NH3 (2M in MeOH), 10:10:2) to give the title compound.

Workup

  1. extractionThe reaction mixture was extracted with CH2Cl2
  2. dry with materialThe organic fraction was dried over Na2CO3
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chromatography (silica, CH2Cl2: ethyl acetate: NH3 (2M in MeOH), 10:10:2)

Sources & evidence

ORD record
ord-b4e7d15a785447a796b4b8301f56b725
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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