Ammonium Chloride → HCID 178514586, compound

HRID 1191299Notes

Reaction equation

HRID 1191299 reaction equation
[N:1]1([C:8]2[CH:13]=[C:12]([Cl:14])[N:11]=[C:10]([NH:15][C@H:16]3[CH2:20][CH2:19][N:18]([CH:21]4[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]4)[C@@H:17]3[CH2:28][CH2:29][CH2:30][N:31]=[N+:32]=[N-:33])[N:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].[Cl-].[NH4+]>O1CCCC1>[N:1]1([C:8]2[CH:13]=[C:12]([Cl:14])[N:11]=[C:10]([NH:15][C@H:16]3[CH2:20][CH2:19][N:18]([C@@H:21]4[CH2:26][CH2:25][C@H:24]([OH:27])[CH2:23][CH2:22]4)[C@@H:17]3[CH2:28][CH2:29][CH2:30][N:31]=[N+:32]=[N-:33])[N:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 3611392Lithium tri-s-butylborohydrideHCID 86634391HCID 86634391, compound

Product 1

HCID 178514586HCID 178514586, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound 45 (1.12 g), tetrahydrofuran (25 mL) and 1.02 mol/L L-Selectride (7.0 mL) were stirred at −78° C. for 1 hour. The reaction solution was added aqueous saturated ammonium chloride solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate:methanol=50:50:0→0:100:0→0:90:10) to obtain the title compound (237 mg) having the following physical properties.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate:methanol=50:50:0→0:100:0→0:90:10)

Sources & evidence

ORD record
ord-7db1910d3ac647dbae07cc7bfe8ebd2f
Source dataset
uspto-grants-2014_03
Patent number
US08680092B2

Reaction notes

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