1,2,3,4-Tetrahydroisoquinoline → HCID 11584930, compound

HRID 1445987Notes

Reaction equation

HRID 1445987 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].[CH2:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:35][CH2:34][NH: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:33]4[CH2:34][CH2:35][C:36]5[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=5)[CH2:32]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 70461,2,3,4-TetrahydroisoquinolineHCID 986734017beta-Hydroxy wortmannin

Product 1

HCID 11584930HCID 11584930, compoundYield 13.3%

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 32 mg (0.24 mmol) 1,2,3,4-tetrahydroisoquinoline. The reaction mixture is stirred at room temperature overnight. CH2Cl2 is removed in vacuo. The residue is triturated with Et2O to give 9 mg (13.3%) product as an orange powder. MS (ESI) m/z 564.25 (M+1).

Workup

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

Sources & evidence

ORD record
ord-08b8ac808b8a49648191b43d501ae401
Source dataset
uspto-grants-2010_02
Patent number
US07666901B2

Reaction notes

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