Phenylacetyl chloride → (3aR,7aR)-7,7-Diphenyl-2-(phenylacetyl)perhydro-4-isoindolone

HRID 1029873Notes

Reaction equation

HRID 1029873 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl.[C:19]1([C:25]2([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@H:33]3[C@H:29]([CH2:30][NH:31][CH2:32]3)[C:28](=[O:34])[CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)(O)[O-].[Na+]>ClCCl>[C:35]1([C:25]2([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C@H:33]3[C@H:29]([CH2:30][N:31]([C:8](=[O:9])[CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH2:32]3)[C:28](=[O:34])[CH2:27][CH2:26]2)[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 22843247(3aR,7aR)-7,7-diphenyl-4-perhydroisoindolone hydrochloride

Product 1

HCID 22843240(3aR,7aR)-7,7-Diphenyl-2-(phenylacetyl)perhydro-4-isoindolone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of phenylacetyl chloride (4 cc) and triethylamine (8.6 cc) in dichloromethane (10 cc) is added dropwise to a solution of (3aR,7aR)-7,7-diphenyl-4-perhydroisoindolone hydrochloride (10 g) in dry dichloromethane (80 cc) cooled to +5° C. The reaction mixture is stirred for 2 hours at +5° C. and then for 20 hours at 20° C. The reaction mixture is treated with a saturated aqueous solution (30 cc) of sodium bicarbonate; the organic phase is washed with distilled water (2 * 50 cc), dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized from acetonitrile (15 cc). The crystals are drained, washed with acetonitrile (10 cc) and with isopropyl ether (10 cc) and dried. (3aR,7aR)-7,7-diphenyl-2-(phenylacetyl)-4-perhydroisoindolone (5.7 g) melting at 173° C. is obtained; [a]D20 =-282° (c=1, methanol).

Workup

  1. temperaturecooled to +5° C
  2. waitfor 20 hours at 20° C
  3. washthe organic phase is washed with distilled water (2 * 50 cc)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe residue is crystallized from acetonitrile (15 cc)
  8. washwashed with acetonitrile (10 cc) and with isopropyl ether (10 cc)
  9. customdried

Sources & evidence

ORD record
ord-5a04e955ef524053abcf1191b0d72169
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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