Tetrahydrofuran → HCID 70656194, compound

HRID 1972486Notes

Reaction equation

HRID 1972486 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:27])([CH3:26])[C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)[C@@H:11]([CH2:28][N:29]2[CH:34]3[CH2:35][C:36](=[O:38])[CH2:37][CH:30]2[CH2:31][O:32][CH2:33]3)[CH2:10]1)(=[O:8])=[O:7].C1COCC1.[BH4-].[Na+]>CO>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:27])([CH3:26])[C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)[C@@H:11]([CH2:28][N:29]2[CH:30]3[CH2:37][CH:36]([OH:38])[CH2:35][CH:34]2[CH2:33][O:32][CH2:31]3)[CH2:10]1)(=[O:7])=[O:8]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 665823999-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-oxa-9-azabicyclo[3.3.1]nonan-7-one

Product 1

HCID 70656194HCID 70656194, compoundYield 15.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 25-mL round-bottomed flask was charged with 9-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-oxa-9-azabicyclo[3.3.1]nonan-7-one (60 mg, 0.11 mmol, Example 106), THF (3 mL) and MeOH (0.5 mL). NaBH4 (39.6 mg, 1.05 mmol) was added and the reaction stirred at room temperature for 20 min. MeOH (50 mL) was added and then the mixture was concentrated onto silica gel and purified via column chromatography (12 g silica gel, 0 to 10% MeOH in CH2Cl2) to give 9-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)-3-oxa-9-azabicyclo[3.3.1]nonan-7-ol (endo) (10 mg) as a mixture of two isomers.

Workup

  1. concentrationthe mixture was concentrated onto silica gel
  2. custompurified via column chromatography (12 g silica gel, 0 to 10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-67cc812469aa4f64b16114d5b94569dd
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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