Methylamine → HCID 59253237, compound

HRID 386891Notes

Reaction equation

HRID 386891 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[O:12][N:11]=[C:10]([C:13]([CH3:17])([CH3:16])[CH:14]=O)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:19][NH2:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C>C1COCC1>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[O:12][N:11]=[C:10]([C:13]([CH3:17])([CH3:16])[CH2:14][NH:20][CH3:19])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 2724942TriacetoxyborohydrideHCID 59253218[3-(1,1-Dimethyl-2-oxo-ethyl)-isoxazol-5-yl]-carbamic acid tert-butyl ester

Product 1

HCID 59253237HCID 59253237, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

[3-(1,1-Dimethyl-2-oxo-ethyl)-isoxazol-5-yl]-carbamic acid tert-butyl ester (150.0 mg, 0.59 mmol) is dissolved in THF (1.0 mL) and 2M methylamine in THF (0.35 mL, 0.71 mmol) is added followed by the addition of MP-triacetoxyborohydride (546.0 mg, 2.70 mmol/g). The reaction mixture is placed on a shaker for 2 h. After this time, the reaction mixture is filtered and the filtrate is concentrated under reduced pressure to provide 163.0 mg of the title compound which is used crude for the next step. m/z 270 [M+H].

Workup

  1. filtrationAfter this time, the reaction mixture is filtered
  2. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-760c7d9c02804376b3233a31443e66cb
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

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