Borane;tetrahydrofuran → HCID 69287441, compound

HRID 2250318Notes

Reaction equation

HRID 2250318 reaction equation
B.C1COCC1.[CH2:7]([O:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][CH2:25][C:26]([NH2:28])=O)[CH2:19][CH2:18]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[CH2:7]([O:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][CH2:25][CH2:26][NH2:28])[CH2:19][CH2:18]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 692864584-[1-(2-Benzyloxyethyl)piperidin-4-yl]butyramide

Product 1

HCID 69287441HCID 69287441, compoundYield 97.8%

Procedure

To a solution of BH3.THF (2.2 mL, 2.2 mmol) cooled to 0° C. was added compound 4a (100 mg, 0.3 mmol). The resulting mixture was stirred for 30 min, then warmed to room temperature and stirred overnight. The reaction was quenched with water, and extracted with Et2O. The organic solution was dried over Na2SO4 and concentrated under vacuum to provide 5a (85.2 mg, 89%) which was used directly without further purification. 1H NMR (500 MHz, CD3OD) δ 1.39 (m, 2H), 1.45 (m, 4H), 1.62 (m, 1H), 1.71 (m, 2H), 1.95 (m, 2H), 2.87 (m, 2H), 2.97 (m, 2H), 3.25 (m, 2H), 3.45 (d, 2H), 3.82 (m, 2H), 4.61 (s, 2H), 7.39 (m, 5H). m/z (ESI): 291 [C18H30N2O+H]+.

Workup

  1. stirringstirred overnight
  2. customThe reaction was quenched with water
  3. extractionextracted with Et2O
  4. dry with materialThe organic solution was dried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-af53c92826514905aae82b35b0246318
Source dataset
uspto-grants-2008_01
Patent number
US07317013B2

Reaction notes

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