Tetrahydrofuran → HCID 86652000, compound

HRID 1423134Notes

Reaction equation

HRID 1423134 reaction equation
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH2:33][CH3:34])CC)C.C([CH:37]([CH2:41][C:42](Cl)=[O:43])[C:38](Cl)=[O:39])C.C1C[O:48]CC1>>[CH2:1]([C@H:8]1[CH2:9][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:12][N:13]1[C:42](=[O:43])[CH2:41][CH2:37][C:38]([O:39][CH2:33][CH3:34])=[O:48])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 16725642(S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazineHCID 218646082-Ethylbutanedioyl dichloride

Product 1

HCID 86652000HCID 86652000, compoundYield 93%

Procedure

A solution of (S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (550 mg, 1.5 mmol) in THF (10 mL) was treated with triethylamine (231 μL, 1.65 mmol) followed by ethylsuccinyl chloride (223 μL, 1.58 mmol). The reaction mixture was stirred for 3 h then partitioned between EtOAc (10 mL) and a saturated aqueous solution of NaHCO3 (10 mL). The organic extract was dried over MgSO4, filtered, and evaporated to an oil, which was purified by silica gel flash chromatography with 25%, 30%, then 40% EtOAc/hexanes as eluant to afford intermediate (S)-ethyl 4-(2-benzyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)piperazin-1-yl)-4-oxobutanoate as a yellow liquid (690 mg, 93%). LC/MS (Method A) 7.49 min, [M+1]+ 495.

Workup

  1. customthen partitioned between EtOAc (10 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried over MgSO4
  4. filtrationfiltered
  5. customevaporated to an oil, which
  6. customwas purified by silica gel flash chromatography with 25%, 30%

Sources & evidence

ORD record
ord-4dbf2eaae5d3495fbcc243052f81ae47
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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