1-Cyclohexylpiperazine → (1E,4S,4aR,5R,6aS,7S)-1-[(4-cyclohexylpiperazin-1-yl)methylene]-7,11-dihydroxy-4-(methoxymethyl)-4a,6a-dimethyl-2,10-dioxo-1,2,4,4a,5,6,6a,7,8,9,9a,10-dodecahydroindeno[4,5-h]isochromen-5-yl acetate

HRID 1445982Notes

Reaction equation

HRID 1445982 reaction equation
[CH3:1][C:2]([O:4][C@H:5]1[C:14]2[C@@:15]3([CH3:30])[C@@H:26]([CH2:27][O:28][CH3:29])[O:25][C:23](=[O:24])[C:17]4=[CH:18][O:19][C:20]([C:21](=[O:22])[C:13]=2[C@@H:8]2[CH2:9][CH2:10][C@H:11]([OH:12])[C@@:7]2([CH3:31])[CH2:6]1)=[C:16]34)=[O:3].[CH:32]1([N:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>C(Cl)Cl>[C:2]([O:4][C@H:5]1[C:14]2[C@:15]3([CH3:30])[C:16](/[C:17](=[CH:18]\[N:41]4[CH2:42][CH2:43][N:38]([CH:32]5[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]5)[CH2:39][CH2:40]4)/[C:23](=[O:24])[O:25][C@@H:26]3[CH2:27][O:28][CH3:29])=[C:20]([OH:19])[C:21](=[O:22])[C:13]=2[CH:8]2[C@@:7]([CH3:31])([C@@H:11]([OH:12])[CH2:10][CH2:9]2)[CH2:6]1)(=[O:3])[CH3:1]

Participants

4

Reactant 2

HCID 872981-CyclohexylpiperazineHCID 986734017beta-Hydroxy wortmannin

Product 1

HCID 11642863(1E,4S,4aR,5R,6aS,7S)-1-[(4-cyclohexylpiperazin-1-yl)methylene]-7,11-dihydroxy-4-(methoxymethyl)-4a,6a-dimethyl-2,10-dioxo-1,2,4,4a,5,6,6a,7,8,9,9a,10-dodecahydroindeno[4,5-h]isochromen-5-yl acetateYield 22.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 50 mg (0.12 mmol) 17-hydroxywortmannin in 0.5 mL CH2Cl2 is added 40.4 mg (0.24 mmol) 1-cyclohexylpiperazine. The reaction mixture is stirred at room temperature overnight. CH2Cl2 is removed in vacuo. The residue is triturated with Et2O to give 16 mg (22%) product as an orange powder. MS (ESI) m/z 599.35 (M+1).

Workup

  1. customCH2Cl2 is removed in vacuo
  2. customThe residue is triturated with Et2O

Sources & evidence

ORD record
ord-83dbed54d3934739b4fa6d391779a4a3
Source dataset
uspto-grants-2010_02
Patent number
US07666901B2

Reaction notes

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