Acetic Acid → HCID 69419930, compound

HRID 456457Notes

Reaction equation

HRID 456457 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH:21]2[CH2:24][NH:23][CH2:22]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:25](O)(=O)C.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH:21]2[CH2:22][N:23]([CH3:25])[CH2:24]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 694173141,1-Dimethylethyl 4-[2-(3-azetidinyloxy)phenyl]-1-piperazinecarboxylate

Product 1

HCID 69419930HCID 69419930, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

4-[2-(Azetidin-3-yloxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester (Preparation 47A, Step 4) (140 mg, 0.42 mmol) was dissolved in CH2Cl2 (2 mL). Acetic acid (0.15 mL) and formalin (85 μL, 1.05 mmol) were added, and the mixture was cooled to 0° C. Sodium triacetoxyborohydride (249 mg, 1.17 mmol) was added, and the solution was stirred for about 16 hours. Methylene chloride (15 mL) was added, and the solution was washed with saturated NaHCO3 (5 mL) and brine (5 mL) and then dried over magnesium sulfate and concentrated to a colorless oil (300 mg, 21%).

Workup

  1. washthe solution was washed with saturated NaHCO3 (5 mL) and brine (5 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated to a colorless oil (300 mg, 21%)

Sources & evidence

ORD record
ord-2b6063a65d254684916a6e49e5b4fafb
Source dataset
uspto-grants-2007_03
Patent number
US07186715B2

Reaction notes

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