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Triethylamine → (2S,4R)-2-(2-hydroxyethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 346360
Notes
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Reaction equation

HRID 346360 reaction equation
[C:1]([CH2:4][O:5][CH2:6][C@@H:7]1[CH2:11][C@@H:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:9][N:8]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1)=[O:18])(O)=[O:2].C(N(CC)CC)C.ClC(OCC(C)C)=O>O1CCCC1>[OH:2][CH2:1][CH2:4][O:5][CH2:6][C@@H:7]1[CH2:11][C@@H:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:9][N:8]1[C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=1)=[O:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 18631935(2S,4R)-2-(carboxymethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 18641547(2S,4R)-2-(2-hydroxyethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidineYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of (2S,4R)-2-(carboxymethyloxymethyl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (2.4 g) in tetrahydrofuran (50 ml) was added triethyamine (1.6 -ml). Isobutyl chloroformate (1.1 ml) was dropwise added to the mixture at -5° to -10° C. under nitrogen, followed by stirring for 30 minutes at the same temperature The insoluble material was filtered off and the filtrate was added to a solution of sodium borohydride (0.70 g) in water (20 ml) at 0° C. After stirring for 2 hours at the same temperature, acetic acid (3 ml) was added thereto The reaction mixture was evaporated, diluted with ethyl acetate and washed successively with water, saturated sodium bicarbonate and brine The dried organic layer was concentrated under reduced pressure, and the obtained syrup was subjected to a column chromatography on silica gel and eluted with a mixture of dichloromethane and acetone (4:1 v/v) to give (2S,4R)-2-(2-hydroxyethyloxymethyl)-4-methane- sulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (2.1 g).

Workup

  1. filtrationwas filtered off
  2. additionthe filtrate was added to a solution of sodium borohydride (0.70 g) in water (20 ml) at 0° C
  3. stirringAfter stirring for 2 hours at the same temperature, acetic acid (3 ml)
  4. additionwas added
  5. customThe reaction mixture was evaporated
  6. additiondiluted with ethyl acetate
  7. washwashed successively with water, saturated sodium bicarbonate and brine The dried organic layer
  8. concentrationwas concentrated under reduced pressure
  9. washeluted with a mixture of dichloromethane and acetone (4:1 v/v)

Sources & evidence

ORD record
ord-7ce06d6109ac46cb8ebe070a3f35d933
Source dataset
uspto-grants-1991_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05061804

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes