Borane;tetrahydrofuran → HCID 15979553, compound

HRID 656506Notes

Reaction equation

HRID 656506 reaction equation
O=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[C:4]2([CH2:17][CH2:16][CH2:15][N:14]3[CH:18]=[N:19][CH:20]=[C:13]23)[NH:3]1.B.O1CCCC1>O1CCCC1>[C:4]12([CH2:17][CH2:16][CH2:15][N:14]3[CH:18]=[N:19][CH:20]=[C:13]13)[C:5]1[C:10](=[CH:9][C:8]([C:11]#[N:12])=[CH:7][CH:6]=1)[CH2:2][NH:3]2

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 15979550HCID 15979550, compound

Product 1

HCID 15979553HCID 15979553, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1.0 mmol of 3′-oxo-2′,3′,6,7-tetrahydro-5H-spiro[imidazo[1,5-a]pyridine-8,1′-isoindole]-5′-carbonitrile (Example 13) in 10 ml of tetrahydrofuran are added 3.0 mmol of a solution of borane-tetrahydrofuran complex (1M in tetrahydrofuran). The reaction mixture is stirred over night at 50° C., then cooled to room temperature and quenched carefully with 10 ml of methanol. After the gas evolution ceases, the reaction mixture is evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60F) on the basis of the Rf value.

Workup

  1. temperaturecooled to room temperature
  2. customquenched carefully with 10 ml of methanol
  3. customAfter the gas evolution ceases, the reaction mixture is evaporated

Sources & evidence

ORD record
ord-f3892dbd1a9b4627b3534965eff2638c
Source dataset
uspto-grants-2011_12
Patent number
US08071774B2

Reaction notes

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