Ammonium Acetate → HCID 131730337, compound

HRID 1948343Notes

Reaction equation

HRID 1948343 reaction equation
[C:1]([BH3-])#[N:2].[Na+].[CH3:5][S:6][CH:7]1C(=O)[CH2:11][CH2:10][N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8]1.C([O-])(=O)C.[NH4+]>CO>[C:17]([O:16][C:14]([N:9]1[CH2:10][CH2:11][C@H:1]([NH2:2])[C@H:7]([S:6][CH3:5])[CH2:8]1)=[O:15])([CH3:18])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 68517449HCID 68517449, compound2×

Product 1

HCID 131730337HCID 131730337, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (344 mg, 5.48 mmol) was added to a solution of tert-butyl 3-(methylthio)-4-oxopiperidine-1-carboxylate (Intermediate 183, 1.07 g, 4.40 mmol), ammonium acetate (3.24 g, 42 mmol) and methanol (15 ml). The resultant mixture was stirred for 4 h. The reaction was quenched by addition of 1N HCl (3 ml). Aqueous sodium bicarbonate (saturated, 50 ml) was added slowly to the reaction mixture followed by extraction with ethyl acetate (3×75 ml). The combined organic phase was dried over sodium sulfate, filtered and concentrated under reduced pressure to yield the crude amine

Workup

  1. customThe reaction was quenched by addition of 1N HCl (3 ml)
  2. additionAqueous sodium bicarbonate (saturated, 50 ml) was added slowly to the reaction mixture
  3. extractionfollowed by extraction with ethyl acetate (3×75 ml)
  4. dry with materialThe combined organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5cb22778d5cd4120b040c1e100f3cee5
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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