Methanol → HCID 71008040, compound

HRID 2361719Notes

Reaction equation

HRID 2361719 reaction equation
O=[C:2]1[CH:10]2[CH2:11][C:6]3([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:7][CH:8]([CH2:12][CH:4]([CH2:5]3)[NH:3]1)[CH2:9]2.CO>C1COCC1>[C:6]12([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH2:11][CH:10]3[CH2:9][CH:8]([CH2:12][CH:4]([NH:3][CH2:2]3)[CH2:5]1)[CH2:7]2

Participants

4

Reactant 2

HCID 887MethanolHCID 71038081HCID 71038081, compound

Product 1

HCID 71008040HCID 71008040, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.0 M solution of BH3-Me2S in THF (1 5 mmol) was added dropwise to a solution of amide 14B (0.125 mmol) in THF (5 mL). The reaction mixture was heated at reflux for 2 h and was allowed to cool to rt. MeOH (2 mL) was cautiously added and the reaction mixture was concentrated. The residue was triturated with DCM (3×10 mL) and the combined organic layers were dried (Na2SO4) and concentrated to provide amine 15A. The amine was used in the next step without further purification. Data: LC/MS (ESR) m/z 167 [M+1]+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. concentrationthe reaction mixture was concentrated
  4. customThe residue was triturated with DCM (3×10 mL)
  5. dry with materialthe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c8c7a178706a41e49250371fbb3ff914
Source dataset
uspto-grants-2014_04
Patent number
US08691808B2

Reaction notes

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