Methylamine → HCID 57904874, compound

HRID 1093058Notes

Reaction equation

HRID 1093058 reaction equation
[Si:1]([O:8][CH2:9][CH:10]1[CH2:14][CH2:13][CH:12]([CH:15]=O)[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:17][NH2:18].[C-:19]#[N:20].[K+]>O.CO>[Si:1]([O:8][CH2:9][CH:10]1[CH2:14][CH2:13][CH:12]([CH:15]([NH:20][CH3:19])[C:17]#[N:18])[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 9032Potassium CyanideHCID 57905221HCID 57905221, compound

Product 1

HCID 57904874HCID 57904874, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
23 °C

Procedure

To 3-((tert-butyldimethylsilyloxy)methyl)-cyclopentanecarbaldehyde (5.8 g, 23.94 mmol) in H2O (8 mL) and methanol (10 mL) was added methylamine (0.0755 g, 23.94 mmol) at 0° C. This mixture was then added at 0° C. to KCN (1.56 g, 23.94 mmol) in H2O (3 mL). The resulting reaction mixture was stirred at 23° C. for 18 hours. The organic material was extracted with ethyl acetate (3×100 mL) and the combined organic fractions were dried (MgSO4) and concentrated in vacuo. 1H NMR (400 MHz, CDCl3) δ ppm 4.27-4.38 (2 H, m), 3.49-3.60 (1 H, m), 2.55 (3 H, s), 2.00-2.35 (4 H, m), 1.65-1.96 (2 H, m), 1.42-1.54 (2 H, m), 1.22 (1 H, ddd, J=13.4, 9.3, 3.8 Hz), 0.89 (9 H, s), 0.05 (6 H, m). LCMS (+ESI, M+H+) m/z 283.

Workup

  1. customThe resulting reaction mixture
  2. extractionThe organic material was extracted with ethyl acetate (3×100 mL)
  3. dry with materialthe combined organic fractions were dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eaef349624c140d4963878369328d717
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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