Borane;tetrahydrofuran → HCID 67165309, compound

HRID 553292Notes

Reaction equation

HRID 553292 reaction equation
B.O1CCCC1.[CH2:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][N:8]1[CH2:16][C:17]1[CH:18]=[C:19]([C:23]2[CH:28]=[CH:27][C:26]([CH2:29][C:30](O)=[O:31])=[CH:25][CH:24]=2)[CH:20]=[CH:21][CH:22]=1>O1CCCC1>[CH2:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][N:8]1[CH2:16][C:17]1[CH:18]=[C:19]([C:23]2[CH:24]=[CH:25][C:26]([CH2:29][CH2:30][OH:31])=[CH:27][CH:28]=2)[CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 67166102HCID 67166102, compound

Product 1

HCID 67165309HCID 67165309, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-tetrahydrofuran complex (1M in tetrahydrofuran) (1.0 mL) was added to a solution of [3′-(1,3-dihydro-iso-indol-2-ylmethyl)-biphenyl-4-yl]-acetic acid (0.444 g) in tetrahydrofuran (30 mL) and stirred at room temperature, under nitrogen, for 3 hours, then evaporated The residue was dissolved in methanol and loaded onto a conditioned SCX cartridge (10 g Varian). The cartridge was washed with methanol (3×20 mL) and then eluted with methanolic ammonia solution (2×20 mL). The combined eluents were concentrated to give the subtitle compound as a dark brown oil (165 mg)

Workup

  1. customevaporated The residue
  2. dissolutionwas dissolved in methanol
  3. washThe cartridge was washed with methanol (3×20 mL)
  4. washeluted with methanolic ammonia solution (2×20 mL)
  5. concentrationThe combined eluents were concentrated

Sources & evidence

ORD record
ord-6d8272bf4f874e68ac4440d497166791
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Reaction notes

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