Hydrogen chloride-ethyl acetate → Benzyl (azetidin-3-ylmethyl)carbamate hydrochloride

HRID 43911Notes

Reaction equation

HRID 43911 reaction equation
[ClH:1].C(OCC)(=O)C.[CH2:8]([O:15][C:16]([NH:18][CH2:19][CH:20]1[CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1CCOCC1.CO>[ClH:1].[CH2:8]([O:15][C:16]([NH:18][CH2:19][CH:20]1[CH2:23][NH:22][CH2:21]1)=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 45072305tert-Butyl 3-((((benzyloxy)carbonyl)amino)methyl)azetidine-1-carboxylate

Product 1

HCID 44828569Benzyl (azetidin-3-ylmethyl)carbamate hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 21966525Dioxane MethanolSolvent

Procedure

A 4 N hydrochloric acid/ethyl acetate solution (3.90 mL, 15.6 mmol) was added to a solution of tert-butyl 3-({[(benzyloxy)carbonyl]amino}methyl)azetidine-1-carboxylate obtained in Example (233a) (560 mg, 1.75 mmol) in 1,4-dioxane/methanol (8 mL/8 mL), and the mixture was stirred at room temperature for 4.5 hours. The reaction solution was concentrated to obtain 448 mg of 3-({[(benzyloxy)carbonyl]amino}methyl)azetidine hydrochloride (100%).

Workup

  1. concentrationThe reaction solution was concentrated

Sources & evidence

ORD record
ord-738fc753cf2042cf95068bc68ce3d2a0
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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