Phthalimide → HCID 70044124, compound

HRID 233637Notes

Reaction equation

HRID 233637 reaction equation
N(C(OCC)=O)=NC(OCC)=O.O[CH2:14][CH2:15][O:16][C@H:17]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@H:19]([CH2:20][CH2:21][C@@H:22]3[C@@H:31]2[CH2:30][CH2:29][C@@:27]2([CH3:28])[C@:23]3([OH:41])[CH2:24][CH2:25][C@@H:26]2[C:36]2[CH:40]=[CH:39][O:38][CH:37]=2)[CH2:18]1.[C:42]1(=[O:52])[NH:46][C:45](=[O:47])[C:44]2=[CH:48][CH:49]=[CH:50][CH:51]=[C:43]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:42]1(=[O:52])[N:46]([CH2:14][CH2:15][O:16][C@H:17]2[CH2:34][CH2:33][C@@:32]3([CH3:35])[C@H:19]([CH2:20][CH2:21][C@@H:22]4[C@@H:31]3[CH2:30][CH2:29][C@@:27]3([CH3:28])[C@:23]4([OH:41])[CH2:24][CH2:25][C@@H:26]3[C:36]3[CH:40]=[CH:39][O:38][CH:37]=3)[CH2:18]2)[C:45](=[O:47])[C:44]2=[CH:48][CH:49]=[CH:50][CH:51]=[C:43]12

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 70043593HCID 70043593, compound

Product 1

HCID 70044124HCID 70044124, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.29 ml of diethyl azodicarboxylate was added dropwise, under nitrogen, to a solution of 0.75 g of 3β-(2-hydroxyethoxy)-17β-(3-furyl)-5β-androstan-14β-ol, 0.28 g of phthalimide and 0.50 g of triphenylphosphine in 7 ml of tetrahydrofuran at room temperature. After 2 hrs the solvent was removed in vacuo, the crude product was dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude product was purified by flash-chromatography (SiO2) using n-hexane/ethyl acetate 80/20 to give 0.70 g of 3β-(2-phthalimidoethoxy)-17β-(3-furyl)-5β-androstan-14β-ol.

Workup

  1. customAfter 2 hrs the solvent was removed in vacuo
  2. dry with materialthe crude product was dried over anhydrous sodium sulfate
  3. customevaporated to dryness under reduced pressure
  4. customThe crude product was purified by flash-chromatography (SiO2)

Sources & evidence

ORD record
ord-baca649f45d847738a6a8a062ada55cc
Source dataset
uspto-grants-1997_01
Patent number
US05593982

Reaction notes

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