Sodium triacetoxyborohydride → HCID 58617764, compound

HRID 916875Notes

Reaction equation

HRID 916875 reaction equation
[S:1]1[CH2:6][CH2:5][CH:4]([CH:7]=O)[CH2:3][CH2:2]1.[CH2:9]([O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:22]3[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=3[N:20]=[C:19]2[C@H:28]([NH2:30])[CH3:29])=[CH:14][CH:13]=1)[CH3:10].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.ClCCl>[CH2:9]([O:11][C:12]1[CH:13]=[CH:14][C:15]([N:18]2[C:22]3[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=3[N:20]=[C:19]2[C@H:28]([NH:30][CH2:7][CH:4]2[CH2:3][CH2:2][S:1][CH2:6][CH2:5]2)[CH3:29])=[CH:16][CH:17]=1)[CH3:10]

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 20143720Thiane-4-carbaldehydeHCID 58617761HCID 58617761, compound

Product 1

HCID 58617764HCID 58617764, compoundYield 49.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

Tetrahydro-thiopyran-4-carbaldehyde (35.80 g, 275.4 mmol) was added to a solution of compound A2 (80.73 g, 270 mmol) in dichloroethane (700 mL) at −20° C., followed by sodium triacetoxyborohydride (85.84 g, 405 mmol). The mixture was kept at that temperature for 4 h. The solution was diluted with dichloromethane, washed by saturated aqueous sodium bicarbonate, water, brine and dried over anhydrous sodium sulfate The solvent was evaporated and the residue was purified by flash column to yield A3 as a yellow solid (55 g). MS(ESI+) 414.1 (MH+).

Workup

  1. washwashed by saturated aqueous sodium bicarbonate, water, brine
  2. dry with materialdried over anhydrous sodium sulfate The solvent
  3. customwas evaporated
  4. customthe residue was purified by flash column

Sources & evidence

ORD record
ord-cb9aafa2155c437d9c32b40235ab0206
Source dataset
uspto-grants-2007_09
Patent number
US07271271B2

Reaction notes

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