Water → (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(2-naphthyl)acetyl]perhydro-4,5-isoindolediol

HRID 1780970

Reaction equation

HRID 1780970 reaction equation
[C:1]1([C:7]2([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:15]3[CH:11]([CH2:12][NH:13][CH2:14]3)[C:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])([OH:16])[CH:9]([OH:25])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.[CH:41]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=[CH:43][C:42]=1[CH2:51][C:52](Cl)=[O:53].O>ClCCl>[C:26]1([C:7]2([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:15]3[CH:11]([CH2:12][N:13]([C:52](=[O:53])[CH2:51][C:42]4[CH:43]=[CH:44][C:45]5[C:50](=[CH:49][CH:48]=[CH:47][CH:46]=5)[CH:41]=4)[CH2:14]3)[C:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])([OH:16])[CH:9]([OH:25])[CH2:8]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 5881152-(2-Naphthyl)acetyl chlorideHCID 19047650(3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol

Product 1

HCID 67718980(3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(2-naphthyl)acetyl]perhydro-4,5-isoindolediolYield 50.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.42 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol in 10 cm3 of dichloromethane is added 0.21 cm3 of diisopropylethylamine, followed by 0.23 g of 2-naphthylacetyl chloride in 5.5 cm3 of dichloromethane. After stirring at room temperature for 1 hour, 25 cm3 of water are added. The organic phase is separated off after settling, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is taken up in 50 cm3 of ethyl acetate, 3 cm3 of 1N aqueous hydrochloric acid and 40 cm3 of water. The organic phase is separated off after settling, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The solid obtained is crystallized a first time in 5 cm3 of 2-propanol and then a second time in 5 cm3 of isopropyl ether. 0.3 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(2-naphthyl)acetyl]perhydro-4,5-isoindolediol is obtained, melting at 188°-190° C.

Workup

  1. customThe organic phase is separated off
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe organic phase is separated off
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe solid obtained
  8. customis crystallized a first time in 5 cm3 of 2-propanol

Sources & evidence

ORD record
ord-fb44ceafc3a5487c9f4702671fd25908
Source dataset
uspto-grants-1997_05
Patent number
US05631279

Linked notes

Loading…