Triethylamine → {(R)-3-[3-(4-chloro-phenoxy)-azetidin-1-yl]-1-methyl-propyl}-carbamic acid tert-butyl ester

HRID 1182105Notes

Reaction equation

HRID 1182105 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][C@H:8]([CH3:12])[CH2:9][CH2:10]I)([CH3:4])([CH3:3])[CH3:2].Cl.[Cl:15][C:16]1[CH:26]=[CH:25][C:19]([O:20][CH:21]2[CH2:24][NH:23][CH2:22]2)=[CH:18][CH:17]=1.C(N(CC)CC)C>CN(C=O)C>[C:1]([O:5][C:6](=[O:13])[NH:7][C@H:8]([CH3:12])[CH2:9][CH2:10][N:23]1[CH2:24][CH:21]([O:20][C:19]2[CH:18]=[CH:17][C:16]([Cl:15])=[CH:26][CH:25]=2)[CH2:22]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 573501973-(4-Chlorophenoxy)azetidine hydrochlorideHCID 86600852((R)-3-iodo-1-methyl-propyl)-carbamic acid tert-butyl ester

Product 1

HCID 69410570{(R)-3-[3-(4-chloro-phenoxy)-azetidin-1-yl]-1-methyl-propyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ((R)-3-iodo-1-methyl-propyl)-carbamic acid tert-butyl ester (0.038 mg, 0.13 mmol), 3-(4-chloro-phenoxy)-azetidine hydrochloride (0.030 g, 0.13 mmol) and triethylamine (0.073 ml, 0.52 mmol) in DMF (1 ml) is stirred at room temperature for 18 hours. The reaction mixture is partitioned between ethylacetate and a saturated solution of sodium bicarbonate. The organic phase is washed with water and brine, dried over magnesium sulphate and evaporated. The crude product is purified by flash silica chromatography using 1:1 ethylacetate:hexane as eluent to afford {(R)-3-[3-(4-chloro-phenoxy)-azetidin-1-yl]-1-methyl-propyl}-carbamic acid tert-butyl ester. [M+H] 355.33

Workup

  1. customThe reaction mixture is partitioned between ethylacetate
  2. washThe organic phase is washed with water and brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe crude product is purified by flash silica chromatography

Sources & evidence

ORD record
ord-976b9e786a4a4e83ac064dc40060e002
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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