Acetic Acid → HCID 67080067, compound

HRID 655535Notes

Reaction equation

HRID 655535 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([NH2:15])[CH2:12][O:13][CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][O:17][CH:18]([O:21][CH3:22])[CH:19]=O.S([O-])([O-])(=O)=O.[Mg+2].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]([NH:15][CH2:19][CH:18]([O:21][CH3:22])[O:17][CH3:16])[CH2:12][O:13][CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 162650Acetaldehyde, 2,2-dimethoxy-2×HCID 5003444Sodium cyanoborohydrideHCID 67080110HCID 67080110, compound

Product 1

HCID 67080067HCID 67080067, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-3-benzyloxy-1-methoxymethyl-propylamine (1.34 g, 6.40 mmol) in methanol (25 mL) were added dimethoxyacetaldehyde solution (45% in tert-butyl methyl ether, 1.81 mL, 7.04 mmol), magnesium sulfate (6.94 g, 57.6 mmol), acetic acid (1.54 g, 25.6 mmol), and sodium cyanoborohydride (551 mg, 8.32 mmol), then after 4 h the reaction mixture was cooled to 0° C. and treated with another portion of dimethoxyacetaldehyde solution (45% in tert-butyl methyl ether, 0.22 mL, 0.96 mmol). The ice bath was removed, then after 2 h the reaction was stopped by careful addition of sat. aq. sodium hydrogencarbonate solution. The reaction mixture was partitioned between sat. aq. sodium hydrogencarbonate solution and ethyl acetate, the organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; dichloromethane/methanol 19:1) furnished the title compound (1.60 g, 84%). Light yellow liquid, MS (ISP)=298.3 (M+H)+.

Workup

  1. customThe ice bath was removed
  2. additionafter 2 h the reaction was stopped by careful addition of sat. aq. sodium hydrogencarbonate solution
  3. customThe reaction mixture was partitioned between sat. aq. sodium hydrogencarbonate solution and ethyl acetate
  4. washthe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-2191bd84e68f4937a3d5e347cd3a34e7
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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