Water → HCID 178449163, compound

HRID 1007531Notes

Reaction equation

HRID 1007531 reaction equation
[CH:1]1([C:8]2[CH:17]=[CH:16][C:11]3[NH:12][C:13](=[O:15])[O:14][C:10]=3[CH:9]=2)[CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.[BH4-].[Na+].O.CCO[C:24]([CH3:26])=O>C1COCC1>[C:1]1([CH:24]([CH3:26])[CH2:10][CH2:11][NH:12][C@H:4]2[CH2:5][CH2:6][C@H:1]([C:8]3[CH:17]=[CH:16][C:11]4[NH:12][C:13](=[O:15])[O:14][C:10]=4[CH:9]=3)[CH2:2][CH2:3]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 98133826-(4-oxocyclohexyl)-1,3-benzoxazol-2(3H)-one

Product 1

HCID 178449163HCID 178449163, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of amine 14 (1.3 g, 6.2 mmol) in THF (75 mL) was added 5 (1.44 g, 6.22 mmol). The reaction mixture was stirred for 1 hour, NaBH4 (329 mg, 8.71 mmol) was added followed by water (30 mL). The reaction mixture was stirred for 45 minutes then diluted with EtOAc. The mixture was washed with 1N HCl and concentrated under reduced pressure. Purification by flash chromatography (silica, 95:5:1 CH2Cl2:MeOH:NH4OH) gave 6-[trans-4-(3-phenylbutylamino)cyclohexyl]-3H-benzoxazol-2-one (640 mg, 28%), as a white solid: 1H NMR (300 MHz, DMSO-d6): δ 7.31-7.11 (m, 7H), 6.94 (s, 1H), 2,78 (m, 1H), 2.45-2.35 (m, 5H), 1.87 (br d, J=10 Hz, 2H), 1.73 (br d, J=10 Hz, 2H), 1.68 (m, 2H), 1.44 (dddd, J=10, 10, 10, 2 Hz, 2H), 1.19 (d, J=4 Hz, 3H), 1.08 (dddd, J=10, 10, 10, 2 Hz, 2H).

Workup

  1. stirringThe reaction mixture was stirred for 45 minutes
  2. washThe mixture was washed with 1N HCl
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash chromatography (silica, 95:5:1 CH2Cl2:MeOH:NH4OH)

Sources & evidence

ORD record
ord-6d2a6804c18245609eb78afc6ad5ac84
Source dataset
uspto-grants-2004_09
Patent number
US06794402B2

Reaction notes

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