Water → HCID 54050595, compound

HRID 618182Notes

Reaction equation

HRID 618182 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH2:9]([O:16][C@H:17]1[C@H:21]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:20][NH:19][CH2:18]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(C)C=CC=CC=1.O>C(OCC)C>[CH2:23]([O:22][C@H:21]1[C@H:17]([O:16][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:18][N:19]([Cl:1])[CH2:20]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 31398ChlorosuccinimideHCID 54361786HCID 54361786, compound

Product 1

HCID 54050595HCID 54050595, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

N-Chlorosuccinimide (7.05 g, 52.6 mmol) was added to a solution of (3R,4R)-3,4-dibenzyloxypyrrolidine (15 g, 52.8 mmol) in diethyl ether (300 ml). The resulting mixture was stirred at room temperature for 3 hours under a nitrogen atmosphere. Addition of toluene (250 ml) and water (200 ml), washing of the organic phase with 2 M sodium thiosufate (200 ml) and water (200 ml), drying with magnesium sulphate gave a solution of (3R,4R)-3,4-dibenzyloxy-1-chloropyrrolidine in toluene. The compound is unstable and was used without further purification.

Workup

  1. washwashing of the organic phase with 2 M sodium thiosufate (200 ml) and water (200 ml)
  2. dry with materialdrying with magnesium sulphate

Sources & evidence

ORD record
ord-e9ce2739396647f9bd63ad2e42e85d28
Source dataset
uspto-grants-1999_09
Patent number
US05952363

Reaction notes

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