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Sodium Azide → (3aS,4S,6R,7aR)-6-azidomethyl-4-(2-methoxyphenyl)-2-[(S)-2-(2-methoxyphenyl)propionyl]perhydroisoindol-4-ol

HRID 1599155
Notes
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Reaction equation

HRID 1599155 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C@:13]1([OH:46])[CH2:21][C@H:20]([CH2:22]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:19][C@@H:18]2[C@H:14]1[CH2:15][N:16]([C:34](=[O:45])[C@H:35]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[O:43][CH3:44])[CH3:36])[CH2:17]2>CN(C)C=O.O>[N:1]([CH2:22][C@@H:20]1[CH2:19][C@@H:18]2[C@@H:14]([CH2:15][N:16]([C:34](=[O:45])[C@H:35]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[O:43][CH3:44])[CH3:36])[CH2:17]2)[C@@:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH3:5])([OH:46])[CH2:21]1)=[N+:2]=[N-:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 22884866(3aS,4S,6R,7aR)-4-(2-methoxyphenyl)-2-[(S)-2-(2-methoxyphenyl)propionyl]-6-tosyloxymethyl perhydroisoindol-4-ol

Product 1

HCID 86752421(3aS,4S,6R,7aR)-6-azidomethyl-4-(2-methoxyphenyl)-2-[(S)-2-(2-methoxyphenyl)propionyl]perhydroisoindol-4-olYield 99.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
20 °C

Procedure

1.68 g of sodium azide are added to a solution, which has been brought to 50° C., of 9.0 g (3aS,4S,6R,7aR)-4-(2-methoxyphenyl)-2-[(S)-2-(2-methoxyphenyl)propionyl]-6-tosyloxymethylperhydroisoindol-4-ol in 50 cm3 of dimethylformamide. The reaction mixture is stirred at 20° C. for 20 hours and then diluted with 350 cm3 of water and subjected to extraction with 100 cm3 of ethyl acetate. The organic phase is washed with 100 cm3 of water, dried over magnesium sulphate and then concentrated to dryness under reduced pressure (2.7 kPa). 7.0 g of (3aS,4S,6R,7aR)-6-azidomethyl-4-(2-methoxyphenyl)-2-[(S)-2-(2-methoxyphenyl)propionyl]perhydroisoindol-4-ol are obtained in the form of a thick white foam.

Workup

  1. extractionsubjected to extraction with 100 cm3 of ethyl acetate
  2. washThe organic phase is washed with 100 cm3 of water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-ceca9afd328b47debff17cb7110ae762
Source dataset
uspto-grants-1998_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05739351

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes