Red-Al → HCID 20598111, compound

HRID 1839232Notes

Reaction equation

HRID 1839232 reaction equation
[C:1]1([NH:7][C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([C:18]3([C:22]4[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=4)[CH2:21][CH2:20][CH2:19]3)=O)[CH2:11]2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.COCCO[AlH2-]OCCOC.[Na+]>C1(C)C=CC=CC=1>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([C:18]2([CH2:16][N:12]3[CH2:13][CH2:14][CH2:15][CH:10]([CH2:8][NH:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH2:11]3)[CH2:19][CH2:20][CH2:21]2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 16684438Red-AlHCID 20598051HCID 20598051, compound

Product 1

HCID 20598111HCID 20598111, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 202 (0.504 mmol, 200 mg) in Toluene (2 mL) at 0° C. was treated with 3.0 M Red-Al (3.5 equiv, 1.76 mmol) under Ar. The reaction mixture stirred for 12 h and returned to 25° C. The reaction mixture was then cooled to 0° C., quenched with 10% aqueous NaOH and extracted with EtOAc (3×25 mL). The organics were dried with NaCl(sat) and Na2SO4(s). The reaction mixture was purified by chromatography (PTLC, SiO2, 20 cm×20 cm, 1 mm, 2:1 hexane-EtOAc) which provided 203 (170 mg, 186 mg theoretical, 91%) as a colorless oil: Rf 0.61 (SiO2, 2:1 hexane-EtOAc); LRMS m/z 368 (M+, C23H29ClN2, requires 368).

Workup

  1. customreturned to 25° C
  2. customquenched with 10% aqueous NaOH
  3. extractionextracted with EtOAc (3×25 mL)
  4. dry with materialThe organics were dried with NaCl(sat) and Na2SO4(s)
  5. customThe reaction mixture was purified by chromatography (PTLC, SiO2, 20 cm×20 cm, 1 mm, 2:1 hexane-EtOAc) which

Sources & evidence

ORD record
ord-a4da1a193af942e8881c3f7a73b9b521
Source dataset
uspto-grants-2004_01
Patent number
US06677332B1

Reaction notes

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