Water → HCID 178483346, compound

HRID 1007523Notes

Reaction equation

HRID 1007523 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][NH:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([C:17]3[CH:26]=[CH:25][C:20]4[NH:21][C:22](=[O:24])[O:23][C:19]=4[CH:18]=3)[CH2:13][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[BH-](OC(C)=O)(OC(C)=O)O[C:30](C)=O.[Na+].[OH-].[Na+]>CO>[CH3:30][N:10]([CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C@H:11]1[CH2:12][CH2:13][C@H:14]([C:17]2[CH:26]=[CH:25][C:20]3[NH:21][C:22](=[O:24])[O:23][C:19]=3[CH:18]=2)[CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 178518606HCID 178518606, compound

Product 1

HCID 178483346HCID 178483346, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 6-[trans-4-(3-phenylpropylamino)cyclohexyl]-3H-benzoxazol-2-one (263 mg, 0.750 mmol) in MeOH (10 mL) was added H2O (0.5 mL) and p-formaldehyde (113 mg, 3.75 mmol). After stirring the reaction mixture for 3 hours, NaBH(OAc)3 was added, and stirring was continued for 12 hours. Solid NaOH was added to give a clear solution, which was then concentrated under reduced pressure. Purification by flash chromatography (silica, 95:4:1 CH2Cl2:MeOH:NH4OH) gave 6-{trans-4-[methyl(3-phenylpropyl)-amino]cyclohexyl}-3H-benzoxazol-2-one (160 mg, 59%), as a white solid: mp 58-62° C.; IR (KBr): 2929, 1774 cm−1; 1H NMR (500 MHz, DMSO-d6): δ 8.97 (br s, 1H), 7.26-7.12 (m, 6H), 6.99-6.98 (m, 2H), 2.63 (m, 2H), 2.57 (t, J=7 Hz, 2H), 2.56 (m, 1H), 2.38 (m, 2H), 2.18 (s, 3H), 1.78 (m, 2H), 1.68 (m, 2H), 1.37 (m, 2H), 1.27 (m, 2H); CI-MS (methane) (m/z): 365 [M+H]+; HRMS-API (m/z): [M+H]+ calcd for C23H28N2O2, 365.2229; found, 365.2231; HPLC: method A, 5.95 minutes (95.3%); method B, 10.12 minutes (97.6%); Anal. Calcd for C23H28N2O2.0.25H2O: C, 74.87; H, 7.79; N, 7.59. Found: C, 74.77; H, 7.71; N, 7.81.

Workup

  1. stirringstirring
  2. waitwas continued for 12 hours
  3. customto give a clear solution, which
  4. concentrationwas then concentrated under reduced pressure
  5. customPurification by flash chromatography (silica, 95:4:1 CH2Cl2:MeOH:NH4OH)

Sources & evidence

ORD record
ord-349539da39324674aedb97ea387b71fa
Source dataset
uspto-grants-2004_09
Patent number
US06794402B2

Reaction notes

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