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Trityl chloride → (2S,4S)-2-hydroxymethyl-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine

HRID 1590470
Notes
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Reaction equation

HRID 1590470 reaction equation
C([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C@H:7]([CH2:23][OH:24])[CH2:6]1)(=O)C.C[O-].[Na+].[C:28]1([C:34](Cl)([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CO.O1CCCC1.C(OCC)(=O)C>[OH:24][CH2:23][C@@H:7]1[CH2:6][C@H:5]([S:4][C:34]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:9][N:8]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[O:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 6456Trityl chlorideHCID 102695344-Nitrobenzyl (2S,4S)-4-(Acetylthio)-2-(hydroxymethyl)pyrrolidine-1-carboxylateHCID 10942334Sodium Methoxide

Product 1

HCID 15056118(2S,4S)-2-hydroxymethyl-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidineYield 94.7%

Reagents, catalysts & solvents 3

HCID 887
Methanol
Solvent
2×
HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,4S)-4-acetylthio-2-hydroxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (15 g) in a mixture of methanol (150 ml) and tetrahydrofuran (150 ml) was added a 28% solution of sodium methoxide in methanol (8.95 ml) under ice-cooling and the mixture was stirred at the same temperature for 10 minutes. To the mixture was added triphenylmethyl chloride (12.39 g) on ice-bath, followed by stirring at the same temperature for 1 hour. The precipitates were filtered off and the filtrate was evaporated in vacuo to give a residue. The residue was dissolved in ethyl acetate (200 ml), washed with water, dried over magnesium sulfate, and concentrated under reduced pressure to give a syrup. The syrup was chromatographed on silica gel (200 g) eluting with a mixture of dichloromethane and acetone (9:1 V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4S)-2-hydroxymethyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine (22.24 g).

Workup

  1. temperaturecooling
  2. stirringby stirring at the same temperature for 1 hour
  3. filtrationThe precipitates were filtered off
  4. customthe filtrate was evaporated in vacuo
  5. customto give a residue
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto give a syrup
  10. customThe syrup was chromatographed on silica gel (200 g)
  11. washeluting with a mixture of dichloromethane and acetone (9:1 V/V)
  12. additionThe fractions containing the desired compound
  13. customwere collected
  14. customevaporated in vacuo

Sources & evidence

ORD record
ord-bab9583988004b88bb47b35ad2df69b0
Source dataset
uspto-grants-1993_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05202437

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes