Acetaldehyde → HCID 68951162, compound

HRID 1941780Notes

Reaction equation

HRID 1941780 reaction equation
C(OC(N1[CH2:11][CH2:10][C@H:9]1[CH2:12][NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=O)(C)(C)C.C(=O)C.[C:24]([BH3-])#[N:25].[Na+].[C:28]([O-])(=O)C.[NH4+]>CO.[Cl-].[Zn+2].[Cl-]>[NH:25]1[CH2:24][CH2:11][CH:10]1[CH2:9][C@@H:12]([NH:13][C:14]1[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=1)[CH3:28]

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 68727357HCID 68727357, compound

Product 1

HCID 68951162HCID 68951162, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

(S)-2-[(4-Chloro-phenylamino)-methyl]-azetidine-1-carboxylic acid tert-butyl ester (0.08 g, 0.27 mmol) was dissolved in methanol (3 ml), then acetaldehyde (0.059 g, 1.35 mmol), zinc chloride (0.147 g, 1.1 mmol) and sodium cyanoborohydride (0.51 g, 0.81 mmol) were added and the mixture was stirred overnight at 40° C. Saturated ammonium acetate solution (10 ml) was added and extracted with ethyl acetate (3×30 ml). The combined organic layers were dried with magnesium sulphate, filtered and concentrated in vacuo. The residue was dissolved in dichloromethane (3 ml) and trifluoroacetic acid (3 ml) was added. Solvent and access trifluoroacetic acid was evaporated, diisopropylethylamine (0.3 ml) was added to liberate the free base and the mixture was purified by flash chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/heptane 1:1) to yield a light yellow gum, (0.022 g, 38%); MS (ISP): 225.1 ((M+H)+.).

Workup

  1. extractionextracted with ethyl acetate (3×30 ml)
  2. dry with materialThe combined organic layers were dried with magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in dichloromethane (3 ml)
  6. additiontrifluoroacetic acid (3 ml) was added
  7. customSolvent and access trifluoroacetic acid was evaporated
  8. additiondiisopropylethylamine (0.3 ml) was added
  9. customthe mixture was purified by flash chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/heptane 1:1)
  10. customto yield a light yellow gum, (0.022 g, 38%)

Sources & evidence

ORD record
ord-452892db53774e7ca52668a40a447599
Source dataset
uspto-grants-2013_03
Patent number
US08389507B2

Reaction notes

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