4-Chloroaniline → HCID 68727357, compound

HRID 1941779Notes

Reaction equation

HRID 1941779 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]([O:13][C:14]([N:16]1[CH2:19][CH2:18][C@H:17]1[CH:20]=O)=[O:15])([CH3:12])([CH3:11])[CH3:10].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO.C(O)(=O)C>[C:9]([O:13][C:14]([N:16]1[CH2:19][CH2:18][C@H:17]1[CH2:20][NH:6][C:5]1[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

7

Reactant 4

HCID 78124-ChloroanilineHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 10487764HCID 10487764, compound

Product 1

HCID 68727357HCID 68727357, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 4-chloro-aniline (0.57 g, 4.5 mmol) in methanol (18 ml) were added acetic acid (2 ml), (S)-2-formyl-azetidine-1-carboxylic acid tert.butyl ester (1.74 g, 9.4 mmol) and after 15 min stirring sodium cyanoborohydride (0.57 g, 9.0 mmol). The resulting suspension was stirred for 2 hours at room temperature. Aqueous sodium bicarbonate solution (20 ml) was added and the mixture was extracted with ethyl acetate (3×20 ml). The combined organic layers were dried with magnesium sulphate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (SiO2: heptane/ethyl acetate=9:1) to yield a colourless oil (0.99 g, 74%); MS (ISP): 297.1 ((M+H)+.); 241.3 ((M−C(CH3)3+H)+.).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×20 ml)
  2. dry with materialThe combined organic layers were dried with magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (SiO2: heptane/ethyl acetate=9:1)

Sources & evidence

ORD record
ord-3a8f350d6496467b9e0cec426a9d6a43
Source dataset
uspto-grants-2013_03
Patent number
US08389507B2

Reaction notes

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