Triethylamine → {(S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-methoxymethyl-propyl}-carbamic acid tert-butyl ester

HRID 1182103Notes

Reaction equation

HRID 1182103 reaction equation
Cl.[Cl:2][C:3]1[CH:13]=[CH:12][C:6]([O:7][CH:8]2[CH2:11][NH:10][CH2:9]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:21]([O:25][C:26](=[O:35])[NH:27][C@H:28]([CH2:32][O:33][CH3:34])[CH2:29][CH2:30]I)([CH3:24])([CH3:23])[CH3:22]>CN(C)C=O>[C:21]([O:25][C:26](=[O:35])[NH:27][C@H:28]([CH2:32][O:33][CH3:34])[CH2:29][CH2:30][N:10]1[CH2:9][CH:8]([O:7][C:6]2[CH:12]=[CH:13][C:3]([Cl:2])=[CH:4][CH:5]=2)[CH2:11]1)([CH3:22])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 573501973-(4-Chlorophenoxy)azetidine hydrochlorideHCID 86600851((s)-3-Iodo-1-methoxymethyl-propyl)-carbamic acid tert-butyl ester

Product 1

HCID 69411661{(S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-methoxymethyl-propyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(4-Chloro-phenoxy)-azetidine hydrochloride (0.669 g, 3.04 mmol), triethylamine (1.7 ml, 12.16 mmol) and [(S)-3-Iodo-1-methoxymethyl-propyl)-carbamic acid tert-butyl ester (1.0 g, 3.04 mmol) in dimethylformamide (10 ml) is stirred at ambient temperature for 18 hours, then partitioned between ethylacetate and water. The ethylacetate phase is washed with saturated aqueous sodium bicarbonate solution and brine, dried over MgSO4 and evaporated. The crude product is purified by flash silica chromatography (elution with a 5:95 methanol/dichloromethane) to afford {(S)-3-[3-(4-Chloro-phenoxy)-azetidin-1-yl]-1-methoxymethyl-propyl}-carbamic acid tert-butyl ester as a clear oil. [MH]+ 385.25.

Workup

  1. custompartitioned between ethylacetate and water
  2. washThe ethylacetate phase is washed with saturated aqueous sodium bicarbonate solution and brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe crude product is purified by flash silica chromatography (
  6. washelution with a 5:95 methanol/dichloromethane)

Sources & evidence

ORD record
ord-7ea520ab8cd241e3bc08c9e2c61fb5ef
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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