Borane;2-methylpropan-2-amine → HCID 178518597, compound

HRID 2294948Notes

Reaction equation

HRID 2294948 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[NH:16][C:15]3=[O:23])[CH2:10][CH2:9]2)[CH2:4][CH2:3]1.B.C(N)(C)(C)C>CO>[OH:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[NH:16][C:15]3=[O:23])[CH2:10][CH2:9]2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 517393Borane;2-methylpropan-2-amineHCID 97968491,3-dihydro-1-{1-[4-oxocyclohex-1-yl]piperidin-4-yl}-2H-benzimidazol-2-one

Product 1

HCID 178518597HCID 178518597, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1,3-dihydro-1-{1-[4-oxocyclohex-1-yl]piperidin-4-yl}-2H-benzimidazol-2-one (100 mg) in methanol (4 mL) at 0° C., under nitrogen, was added tert-butylamine-borane (28 mg). The reaction mixture was stirred at 0° C. for 1 h, then quenched with water (2 mL) and concentrated to remove the methanol. The resulting oil was dissolved in ethyl acetate (50 mL) and the organic solution was washed with saturated sodium carbonate (10 mL), then water (10 mL), then brine (10 mL) and then dried over sodium sulfate. Concentration under reduced pressure yielded trans-1,3-dihydro-1-{1-[4-hydroxycyclohex-1-yl]piperidin-4-yl}-2H-benzimidazol-2-one (75 mg) as a colorless solid: 1H NMR (400 MHz, CD3 OD) 7.42 (m, 1H), 7.04 (m, 3H), 4.28 (m, 1H), 3.50 (m, 1H), 3.09 (m, 2H), 2.45 (m, 5H), 2.03-1.94 (m, 4H), 1.78-1.75 (m, 2H), 1.44-1.26 (m, 4H). The hydrochloride salt was precipitated from diethyl ether/chloroform: analysis calculated for C18H25N3O2.HCl.0.50 H2O.0.70 CHCl3C: 50.54, H: 6.28, N: 9.45; found C: 50.54, H: 6.19, N: 9.64.

Workup

  1. customquenched with water (2 mL)
  2. concentrationconcentrated
  3. customto remove the methanol
  4. dissolutionThe resulting oil was dissolved in ethyl acetate (50 mL)
  5. washthe organic solution was washed with saturated sodium carbonate (10 mL)
  6. dry with materialwater (10 mL), then brine (10 mL) and then dried over sodium sulfate
  7. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-059610ba3f6c411a8439b062122bb1e9
Source dataset
uspto-grants-1997_11
Patent number
US05691323

Reaction notes

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