Benzyl Chloride → HCID 10826398, compound

HRID 888306Notes

Reaction equation

HRID 888306 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[I-].[K+].C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 10826398HCID 10826398, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

180 g of N-tert-butoxycarbonyl-(R)-3-hydroxypyrrolidine was dissolved into 725 g of toluene, followed by adding 31 g of tetra-n-butyl ammonium bromide and 16 g of potassium iodide as a catalyst. Further, after 1924 g of 10% aqueous solution of sodium hydroxide was added and the mixture was heated to 50° C., 158 g of benzyl chloride was dropped. After the reaction finished, the mixture was cooled to 25° C. and an organic layer was washed with water. The resultant organic layer was concentrated, thereby obtaining 244 g of N-tert-butoxycarbonyl-(R)-3-benzyloxypyrrolidine (yield of 92%). A residual quantity of N-tert-butoxycarbonyl-(R)-3-hydroxypyrrolidine with respect to N-tert-butoxycarbonyl-(R)-3-benzyloxypyrrolidine was 1.1 wt %.

Workup

  1. temperaturethe mixture was cooled to 25° C.
  2. washan organic layer was washed with water
  3. concentrationThe resultant organic layer was concentrated

Sources & evidence

ORD record
ord-6dfad99234b0436e8fc5c7fcb7e48bf5
Source dataset
uspto-grants-2012_08
Patent number
US08247578B2

Reaction notes

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