Sodium triacetoxyborohydride → HCID 67025669, compound

HRID 2390559Notes

Reaction equation

HRID 2390559 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][C@@H:4]([CH3:8])[NH:3]1.[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][C:11]=1[CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][C@@H:20]1[CH3:25].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][N:6]2[CH2:5][C@@H:4]([CH3:8])[NH:3][C@@H:2]([CH3:1])[CH2:7]2)=[CH:12][C:11]=1[CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][C@@H:20]1[CH3:25]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 86639071HCID 86639071, compound

Product 1

HCID 67025669HCID 67025669, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2S,6R)-2,6-Dimethylpiperazine (0.304 g, 2.67 mmol) and (S)-4-bromo-3-((3-methylmorpholino)methyl)benzaldehyde (0.530 g, 1.78 mmol) in DCM (10 ml) were stirred at RT under nitrogen for 30 minutes. Sodium triacetoxyborohydride (0.565 g, 2.67 mmol) was then added and the resulting solution was stirred at RT over the weekend. The reaction mixture was quenched with saturated NaHCO3. The reaction mixture was extracted with DCM (×3). The organic layer was dried over MgSO4, filtered and evaporated to afford the sub-title compound as a yellow oil. Yield: 0.620 g

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3
  2. extractionThe reaction mixture was extracted with DCM (×3)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-1773feaab3a4431a9a9003132f93d752
Source dataset
uspto-grants-2012_09
Patent number
US08273774B2

Reaction notes

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