Methylamine → HCID 68744460, compound

HRID 1958751Notes

Reaction equation

HRID 1958751 reaction equation
[CH2:1]([O:7][C:8]1[CH:9]=[C:10]([CH:18]=[CH:19][CH:20]=1)[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C1COCC1.[CH3:26][NH2:27].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>O>[CH2:1]([O:7][C:8]1[CH:9]=[C:10]([CH:18]=[CH:19][CH:20]=1)[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:27][CH3:26])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 86641234HCID 86641234, compound

Product 1

HCID 68744460HCID 68744460, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(3-(hexyloxy)phenoxy)pentanal (72 mg, 0.26 mmol) in 1,2-C12C2H4 (5 mL) was treated with a THF solution of MeNH2 (2.0 M, 0.4 mL, 0.8 mmol). The reaction was stirred in a sealed vial for several min at rt before NaBH(OAc)3 (76 mg, 0.36 mmol) was added in one portion. Again the vial was sealed and stirred at rt for 3 d. The reaction was diluted with H2O and extracted into DCM. The organic extracts were concentrated and the resulting material was purified by preparative TLC on silica gel (5% MeOH:DCM) to afford the title compound as clear oil (17 mg, 23%). 1H NMR (400 MHz, CDCl3) δ ppm 7.15 (t, J=8.21 Hz, 1 H), 6.44-6.51 (m, 3 H), 3.90-3.98 (m, 4 H), 2.64 (t, J=7.07 Hz, 2 H), 2.46 (s, 3 H), 2.28 (br. s, 1 H), 1.72-1.85 (m, 4 H), 1.40-1.67 (m, 6 H), 1.29-1.40 (m, 4 H), 0.91 (t, J=6.57 Hz, 3 H). MS ESI [M+H]+, calcd for [C18H31NO2+H]+: 294.45 found m/z 294.2 (100).

Workup

  1. additionwas added in one portion
  2. customAgain the vial was sealed
  3. extractionextracted into DCM
  4. concentrationThe organic extracts were concentrated
  5. customthe resulting material was purified by preparative TLC on silica gel (5% MeOH:DCM)

Sources & evidence

ORD record
ord-bcda59906d0b4f859c505ce2391df47e
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

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