Methanol → HCID 178449085, compound

HRID 1007532Notes

Reaction equation

HRID 1007532 reaction equation
[C:1]1([CH:7]([CH3:27])[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.[BH4-].[Na+].[OH-].[Na+].[CH3:33]O>>[CH3:33][N:10]([CH2:9][CH2:8][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:27])[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 5

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 178449163HCID 178449163, compound

Product 1

HCID 178449085HCID 178449085, compoundYield 35%

Procedure

To a stirred solution of 6-{trans-4-[3-phenylbutylamino]-cyclohexyl}-3H-benzoxazol-2-one (638 mg, 1.75 mmol) in MeOH (10 mL) containing water (0.5 mL) was added p-formaldehyde (263 mg, 8.76 mmol). The reaction mixture was stirred for 2 hours, and NaBH4 (519 mg, 2.45 mmol) was added. The reaction mixture was stirred for 3 hours. The reaction was treated with solid NaOH until a clear solution resulted and concentrated under reduced pressure. Purification by flash chromatography (95:5:1 CH2Cl2:MeOH:NH4OH) gave 6-[trans-4-(methyl-3-phenylbutylamino)cyclohexyl]-3H-benzoxazol-2-one (231 mg, 35%), as a white solid: mp 61-70° C.; IR (KBr): 2928, 1774 cm−1; 1H NMR (500 MHz, DMSO-d6): δ 7.29-7.12 (m, 7H), 6.97 (s, 1H), 2.76 (m, 1H), 2.49-2.26 (m, 5H), 2.14 (s, 3H), 1.77 (m, 4H), 1.67 (m, 2H), 1.43 (m, 2H), 1.27 (m, 2H), 1.17 (d, J=4 Hz, 3H); API-MS (m/z): 379 [M+H]+; HPLC: method A, 5.99 minutes (94.3%); HPLC: method B, 10.97 minutes (>99%); Anal. Calcd for C24H30N2O2.0.5H2O: C, 74.39; H, 8.06; N, 7.23. Found: C, 74.41; H, 7.90; N, 7.31.

Workup

  1. stirringThe reaction mixture was stirred for 3 hours
  2. customresulted
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash chromatography (95:5:1 CH2Cl2:MeOH:NH4OH)

Sources & evidence

ORD record
ord-f23c6154db374444a6efb2ce6275f533
Source dataset
uspto-grants-2004_09
Patent number
US06794402B2

Reaction notes

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