Potassium bisulfate → rac-(1-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-4-(1-hydroxymethyl-3-oxo-3-piperidin-1-yl-propyl)-[1,4]diazepan-5-one)

HRID 2095537Notes

Reaction equation

HRID 2095537 reaction equation
C[O:2][C:3](=O)[CH:4]([N:14]1[C:20](=[O:21])[CH2:19][CH2:18][N:17]([C:22](=[O:33])/[CH:23]=[CH:24]/[C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)[CH2:16][CH2:15]1)[CH2:5][C:6](=[O:13])[N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[Li+].[BH4-].OS([O-])(=O)=O.[K+]>CCO>[Cl:32][C:27]1[CH:26]=[C:25](/[CH:24]=[CH:23]/[C:22]([N:17]2[CH2:18][CH2:19][C:20](=[O:21])[N:14]([CH:4]([CH2:3][OH:2])[CH2:5][C:6](=[O:13])[N:7]3[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]3)[CH2:15][CH2:16]2)=[O:33])[CH:30]=[CH:29][C:28]=1[Cl:31]

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 4148881Lithium borohydrideHCID 670740682-{4-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-4-oxo-4-piperidin-1-yl-butyric acid methyl ester

Product 1

HCID 58232098rac-(1-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-4-(1-hydroxymethyl-3-oxo-3-piperidin-1-yl-propyl)-[1,4]diazepan-5-one)Yield 97.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A cooled (0° C.) solution of 0.150 g (0.29 mmol) of 2-{4-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-4-oxo-4-piperidin-1-yl-butyric acid methyl ester in 3.7 ml of EtOH was treated with 0.013 g (0.59 mmol) of LiBH4 (in 3 portions during 48 h until to the end of the reaction). The mixture was stirred at RT for 48 h, cooled to 0° C. and aqueous 10% KHSO4 solution was slowly added. The mixture was partitioned between aqueous saturated NaHCO3/EtOAc (3×). The organic phases were dried (Na2SO4) and evaporated to give 0.136 g (96%) of the titled compound as white foam. MS: 482.2 (MH+, 2Cl).

Workup

  1. customuntil to the end of the reaction)
  2. temperaturecooled to 0° C.
  3. customThe mixture was partitioned between aqueous saturated NaHCO3/EtOAc (3×)
  4. dry with materialThe organic phases were dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-d5cf8ac1e2c7485083fbfb56d68832f6
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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