Borane → HCID 28814419, compound

HRID 2273724Notes

Reaction equation

HRID 2273724 reaction equation
[CH3:1][N:2]([CH3:23])[C:3](=O)[CH2:4][C@H:5]([NH:11]C(=O)OCC1C=CC=CC=1)[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1.B>O1CCCC1>[CH3:23][N:2]([CH3:1])[CH2:3][CH2:4][C@@H:5]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[NH2:11]

Participants

4

Reactant 2

HCID 6331BoraneHCID 131730914HCID 131730914, compound

Product 1

HCID 28814419HCID 28814419, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of EXAMPLE 161B (400 mg) and borane in tetrahydrofuran (1M, 2.5 mL) in tetrahydrofuran (6 mL) was stirred for 24 hours. The reaction was quenched with methanol, taken up in pH 7 buffer solution, and extracted three times with ethyl acetate. The combined extracts were washed with brine and concentrated. The crude product was taken up in HBr in acetic acid (1.1 mL) and stirred for 2 hours. The reaction was poured into CH2Cl2 (50 mL) and washed with 1M NaOH solution. The organic layer was dried over Na2SO4, and concentrated.

Workup

  1. customThe reaction was quenched with methanol
  2. extractionextracted three times with ethyl acetate
  3. washThe combined extracts were washed with brine
  4. concentrationconcentrated
  5. additionThe reaction was poured into CH2Cl2 (50 mL)
  6. washwashed with 1M NaOH solution
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-325890848db845ea8807e8789e832578
Source dataset
uspto-grants-2015_09
Patent number
US09125913B2

Reaction notes

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