2-(tert-Butylamino)ethanol → (1E,4S,4aR,5R,6aS,7S)-1-{[tert-butyl(2-hydroxyethyl)amino]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 1445979Notes

Reaction equation

HRID 1445979 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].[C:32]([NH:36][CH2:37][CH2:38][OH:39])([CH3:35])([CH3:34])[CH3:33]>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:36]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:37][CH2:38][OH:39])/[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 783612-(tert-Butylamino)ethanolHCID 986734017beta-Hydroxy wortmannin

Product 1

HCID 11519606(1E,4S,4aR,5R,6aS,7S)-1-{[tert-butyl(2-hydroxyethyl)amino]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 48.7%

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 28.1 mg (0.24 mmol) 2-(tert-butylamino)-ethanol. The reaction mixture is stirred at room temperature overnight. CH2Cl2 is removed in vacuo. The residue is triturated with diethyl ether (Et2O) to give 32 mg (48.7%) product as an orange powder. MS (ESI) m/z 548.3 (M+1).

Workup

  1. customCH2Cl2 is removed in vacuo
  2. customThe residue is triturated with diethyl ether (Et2O)

Sources & evidence

ORD record
ord-c7ffb7f56b914ec7a230738caf7e665d
Source dataset
uspto-grants-2010_02
Patent number
US07666901B2

Reaction notes

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