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Acetic Acid → 3-[(2,4-Dichlorobenzylamino)-methyl]-azetidine-1-carboxylic acid tert-butyl ester

HRID 1435153
Notes
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Reaction equation

HRID 1435153 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][NH2:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:16]=1[CH:17]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][NH:13][CH2:17][C:16]2[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:15]=2[Cl:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 134042,4-DichlorobenzaldehydeHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 10679125Tert-butyl 3-(aminomethyl)azetidine-1-carboxylate

Product 1

HCID 690029773-[(2,4-Dichlorobenzylamino)-methyl]-azetidine-1-carboxylic acid tert-butyl ester
Yield 65.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 3-aminomethyl-azetidine-1-carboxylic acid tert-butyl ester (300 mg, 1.6 mmol), 2,4-dichlorobenzaldehyde (281 mg, 1.61 mmol) and acetic acid (0.09 mL, 1.61 mmol) in 1,2-dichloroethane (16 mL) at 0° C. is added sodium triacetoxy-borohydride (476 mg, 2.25 mmol). The reaction is warmed to ambient temperature and stirred overnight under N2. The reaction mixture is poured on to 2N NaOH (20 mL) and extracted with ethyl acetate (3×). The combined organic extracts are washed with aqueous saturated NaCl, dried (Na2SO4), filtered and concentrated. The crude product is purified by flash chromatography on silica gel eluting with 5% EtOH (10% NH4OH)/chloroform to yield 360 mg (65%) of 3-[(2,4-dichlorobenzylamino)-methyl]-azetidine-1-carboxylic acid tert-butyl ester. 1H NMR (400 MHz, CD3OD) δH: 7.49-7.47 (2H, m), 7.36-7.34 (1H, m), 4.05-4.01 (2H, m), 3.88 (2H, s), 3.64-3.61 (2H, m), 2.8 (2H, m), 2.78-2.74 (1H, m), 1.46 (9H, s). Mass spectrum (ion spray): m/z=345.1 (M+H).

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic extracts are washed with aqueous saturated NaCl
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by flash chromatography on silica gel eluting with 5% EtOH (10% NH4OH)/chloroform

Sources & evidence

ORD record
ord-909bc2b191724333b1458f9363f4df5b
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07615648B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes