Acetic Acid → HCID 69525013, compound

HRID 1373359Notes

Reaction equation

HRID 1373359 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[F:24])[CH:12]([CH3:16])[CH2:13][CH:14]=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:25][NH2:26].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH3:25][NH:26][CH2:14][CH2:13][CH:12]([CH3:16])[CH:11]([S:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9])[C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[F:24]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86601720HCID 86601720, compound

Product 1

HCID 69525013HCID 69525013, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the aldehyde from Step (a) (0.55 g, 1.47 mmol) and methylamine (2M solution in THF, 1.48 ml, 2.95 mmol) in dry dichloromethane (5 ml) was added acetic acid (0.5 ml) followed by sodium triacetoxyborohydride (0.63 g, 2.95 mmol). The mixture was stirred at room temperature for 16 hours before quenching with saturated aqueous sodium bicarbonate solution (10 ml) and separating the phases. The organic phase was dried (MgSO4) and evaporated under reduced pressure to yield as a mixture of diastereoisomers (3RS, 4RS)-N-methyl-[4-(4-chlorobenzenesulfonyl)-4-(2,5-difluorophenyl)-3-methyl-butyl]amine as a gummy yellow solid, which was carried on to the next stage without further purification.

Workup

  1. custombefore quenching with saturated aqueous sodium bicarbonate solution (10 ml)
  2. customseparating the phases
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-97ab566960d14827be22c2fe09fca95c
Source dataset
uspto-grants-2007_01
Patent number
US07161006B2

Reaction notes

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