Borane;tetrahydrofuran → HCID 68934223, compound

HRID 576248Notes

Reaction equation

HRID 576248 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][C:12]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=O)[C:8]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:7]2[CH2:25][CH2:26][CH2:27][O:28][C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1.B.C1COCC1>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH2:12][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[C:8]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:7]2[CH2:25][CH2:26][CH2:27][O:28][C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 68938836HCID 68938836, compound

Product 1

HCID 68934223HCID 68934223, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of EXAMPLE 77A (0.15 g) in THF (10 mL) was added 1M BH3.THF (1.8 mL). The mixture was stirred at room temperature for 16 hours, quenched with methanol (5 mL) and concentrated. The concentrate was dissolved in ethanol (40 mL) and treated with 12N HCl (0.5 mL). After stirring for three hours, the mixture was concentrated, and the concentrate was purified by preparative reverse phase HPLC (Zorbax SB, C-18, 30% to 100% acetonitrile/water/0.1% TFA).

Workup

  1. customquenched with methanol (5 mL)
  2. concentrationconcentrated
  3. dissolutionThe concentrate was dissolved in ethanol (40 mL)
  4. additiontreated with 12N HCl (0.5 mL)
  5. stirringAfter stirring for three hours
  6. concentrationthe mixture was concentrated
  7. customthe concentrate was purified by preparative reverse phase HPLC (Zorbax SB, C-18, 30% to 100% acetonitrile/water/0.1% TFA)

Sources & evidence

ORD record
ord-a350830324134865804ee0290b05c8c6
Source dataset
uspto-grants-2015_05
Patent number
US09035047B2

Reaction notes

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