Sodium Bisulfate → HCID 53952166, compound

HRID 1451381Notes

Reaction equation

HRID 1451381 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:15]1([CH:21]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@H:22]2[C@@H:27]([NH2:28])[CH:26]3[CH2:29][CH2:30][N:23]2[CH2:24][CH2:25]3)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH2:37]([P:39]([C:43]1[CH:44]=[CH:45][C:46]([O:51][CH3:52])=[C:47]([CH:50]=1)[CH:48]=O)([CH2:41][CH3:42])=[O:40])[CH3:38].S(=O)(=O)(O)[O-].[Na+]>C(Cl)Cl.C(Cl)CCl>[C:31]1([CH:21]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C@H:22]2[C@@H:27]([NH:28][CH2:48][C:47]3[CH:50]=[C:43]([P:39]([CH2:41][CH3:42])([CH2:37][CH3:38])=[O:40])[CH:44]=[CH:45][C:46]=3[O:51][CH3:52])[CH:26]3[CH2:29][CH2:30][N:23]2[CH2:24][CH2:25]3)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 516919Sodium BisulfateHCID 5049666Sodium triacetoxyborohydrideHCID 12225560HCID 12225560, compoundHCID 19974687HCID 19974687, compound

Product 1

HCID 53952166HCID 53952166, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (202 mg, 0.95 mmol) was added to a solution of (2S,3S)-2-diphenylmethyl-1-azabicyclo[2.2.2]octane-3-amine (150 mg, 0.51 mmol) and 5-diethylphosphoryl-2-methoxybenzaldehyde (150 mg, 0.55 mmol) dissolved in methylene chloride (5 ml) at rt, and the resulting solution was stirred for 16 h. Ethylene chloride and 1N sodium bisulfate were added to the reaction mixture. After 5 min the organic layer was washed with aq. sodium bicarbonate solution and brine. The extracts were dried over magnesium sulfate, and concentrated by evaporation. The residual oil was purified by following process: (1) silica-gel chromatography (4-14% methanol-methylene chloride), (2) Merck Lobar Li Chroprep NH2 (25-70%), (3) crystallization from diisopropyl ether. The title compound was obtained in a pure form (11 mg). IR (CH2Cl2) 1270 cm-1 1 H NMR δ: 7.66 (ddd, J=13, 8, 2 Hz, 1H), 7.39 (dd, J=13, 2 Hz, 1H), 7.31-7.03 (m, 10H), 6.75 (dd, J=8, 3.5 Hz, 1H), 4.47 (d, 12.2 Hz, 1H), 4.10 (m, 4H), 3.69-3.57 (m, 2H), 3.54 (s, 3H), 3.25-3.10 (m, 1H), 3.19 (d, J=13 Hz, 1H), 1H), 2.87 (dd Hz, 1H), 2.75 (m, 2H), 2.60 (m, 1H), 2.05 (m, 1H), 1.88 (m, 1H), 1.70-1.20 (m, 3H), 1.35 (t, J=7 Hz, 3H), 1.34 (t, J=7 Hz, 3H).

Workup

  1. washAfter 5 min the organic layer was washed with aq. sodium bicarbonate solution and brine
  2. dry with materialThe extracts were dried over magnesium sulfate
  3. concentrationconcentrated by evaporation
  4. customThe residual oil was purified
  5. custom(1) silica-gel chromatography (4-14% methanol-methylene chloride), (2) Merck Lobar Li Chroprep NH2 (25-70%), (3) crystallization from diisopropyl ether

Sources & evidence

ORD record
ord-524e0ad2c56045e38cbcc161519edd1e
Source dataset
uspto-grants-1997_02
Patent number
US05604241

Reaction notes

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