Sodium triacetoxyborohydride → HCID 67025565, compound

HRID 2390557Notes

Reaction equation

HRID 2390557 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[CH2:10][N:11]1[CH2:16][CH2:15][S:14][CH2:13][CH2:12]1.[CH3:17][C@@H:18]1[CH2:23][NH:22][CH2:21][C@H:20]([CH3:24])[NH:19]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:22]2[CH2:21][C@@H:20]([CH3:24])[NH:19][C@@H:18]([CH3:17])[CH2:23]2)=[CH:4][C:3]=1[CH2:10][N:11]1[CH2:16][CH2:15][S:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 86639070HCID 86639070, compound

Product 1

HCID 67025565HCID 67025565, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-bromo-3-(thiomorpholinomethyl)benzaldehyde (0.73 g, 2.43 mmol) in dichloromethane (24.32 ml) was added (2R,6S)-2,6-dimethylpiperazine (0.416 g, 3.65 mmol). The mixture was allowed to stir at RT for 40 minutes before sodium triacetoxyborohydride (0.773 g, 3.65 mmol) was added. The reaction was stirred at RT for 2 hours. The mixture was diluted with dichloromethane and washed with saturated NaHCO3(aq), dried (MgSO4) and evaporated to give the sub-title compound as a pale yellow oil. Yield: 0.92 g

Workup

  1. additionwas added
  2. washwashed with saturated NaHCO3(aq)
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-32cc32c2dbc44750a163f69c65be418e
Source dataset
uspto-grants-2012_09
Patent number
US08273774B2

Reaction notes

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