Hydrochloric Acid → HCID 66817259, compound

HRID 1755105Notes

Reaction equation

HRID 1755105 reaction equation
C(OC([N:8]1[CH2:12][C@H:11]([OH:13])[C@@H:10]([O:14][CH2:15][CH:16]=[CH2:17])[CH2:9]1)=O)(C)(C)C.[ClH:18].O1CCOCC1>C(Cl)Cl>[ClH:18].[CH2:15]([O:14][C@H:10]1[CH2:9][NH:8][CH2:12][C@@H:11]1[OH:13])[CH:16]=[CH2:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 57019319HCID 57019319, compound

Product 1

HCID 66817259HCID 66817259, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3S,4S)-3-Allyloxy-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester synthesized by the method described in the patent literature (DE4234330) (139 mg, 0.57 mmol) was dissolved in methylene chloride (2.4 ml). A 4 N solution of hydrochloric acid in dioxane (0.628 ml, 2.45 mmol) was added and the mixture was stirred at room temperature for two hours. The reaction solution was concentrated under reduced pressure to give (3S,4S)-4-allyloxy-pyrrolidin-3-ol hydrochloride (105 mg). This was used in the next reaction without further purification.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-63581a7bba3741e3a799ee43462729a9
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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