Sodium Bicarbonate → HCID 68726870, compound

HRID 1941777Notes

Reaction equation

HRID 1941777 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[O:9][CH3:10].[C:11]([O:15][C:16]([N:18]1[CH2:24][CH2:23][CH2:22][C@H:19]1[CH:20]=O)=[O:17])([CH3:14])([CH3:13])[CH3:12].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO.C(O)(=O)C>[C:11]([O:15][C:16]([N:18]1[CH2:24][CH2:23][CH2:22][C@H:19]1[CH2:20][NH:6][C:5]1[CH:7]=[CH:8][C:2]([Cl:1])=[C:3]([O:9][CH3:10])[CH:4]=1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 131036924-Chloro-3-methoxyaniline

Product 1

HCID 68726870HCID 68726870, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 4-chloro-3-methoxyaniline (1.57 g, 10.0 mmol) in methanol (27 ml) were added acetic acid (3 ml), N-(tert-butoxycarbonyl)-L-prolinal (2.40 g, 12.05 mmol) and sodium cyanoborohydride (1.56 g, 24.1 mmol). The resulting suspension was stirred for 2 hours at room temperature. Aqueous sodium bicarbonate solution (30 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=70:30) to yield a light yellow oil (2.31 g, 68%); MS (ISP): 341.0, 342.9 ((M+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=70:30)

Sources & evidence

ORD record
ord-98c0362975604a43b340064e3000e776
Source dataset
uspto-grants-2013_03
Patent number
US08389507B2

Reaction notes

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