1,1-Dichloroethane → HCID 58786483, compound

HRID 1376048Notes

Reaction equation

HRID 1376048 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:23]([NH:26][CH:27]([CH3:29])C)(C)C.C(O[BH-](O[C:40](=O)[CH3:41])OC(=O)C)(=O)C.[Na+].Cl[CH:45](Cl)C>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:15][N:26]([CH2:23][CH2:40][CH3:41])[CH2:27][CH2:29][CH3:45])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 63651,1-DichloroethaneHCID 7912DiisopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 58786478HCID 58786478, compound

Product 1

HCID 58786483HCID 58786483, compoundYield 49%

Procedure

To 4-(2-Oxo-1-phenyl-ethyl)-piperazine-1-carboxylic acid tert-butyl ester (206) (0.47 g, 1.56 mmol) in dichloroethane (5 mL) was added diisopropylamine (0.21 mL, 1.56 mmol) and sodium triacetoxyborohydride (0.45 g, 2.15 mmol). The reaction was allowed to stir at room temperature for 18 h. The reaction mixture was then quenched with 5N NaOH (5.6 mL) and diluted with EtOAc. The organic phase was dried with MgSO4 and concentrated to dryness. The crude material was purified by chromatography (silica gel 60 mesh, eluting with 100% EtoAc) yielding 0.30 g (49%) pure product.

Workup

  1. customThe reaction mixture was then quenched with 5N NaOH (5.6 mL)
  2. additiondiluted with EtOAc
  3. dry with materialThe organic phase was dried with MgSO4
  4. concentrationconcentrated to dryness
  5. customThe crude material was purified by chromatography (silica gel 60 mesh, eluting with 100% EtoAc)

Sources & evidence

ORD record
ord-051b6e2249784c9c8638924de5887079
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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