Water → HCID 18379009, compound

HRID 2299001Notes

Reaction equation

HRID 2299001 reaction equation
[CH:1]([CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH:14]3[CH2:16][CH:15]3[C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][CH:26]=3)[CH:23]=[C:22]([C:27]#[N:28])[CH:21]=[CH:20]4)[CH:12]=2)[CH2:7][CH2:6][NH:5]1)([CH3:3])[CH3:2].[CH:29]1([CH:32]=O)[CH2:31][CH2:30]1.C([BH3-])#N.[Na+].O>CO>[CH:29]1([CH2:32][N:5]2[CH2:6][CH2:7][C:8]3[C:13](=[CH:12][C:11]([CH:14]4[CH2:16][CH:15]4[C:17]4[CH:18]=[C:19]5[C:24](=[CH:25][CH:26]=4)[CH:23]=[C:22]([C:27]#[N:28])[CH:21]=[CH:20]5)=[CH:10][CH:9]=3)[CH:4]2[CH:1]([CH3:3])[CH3:2])[CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 962WaterHCID 123114CyclopropanecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 18680150HCID 18680150, compound

Product 1

HCID 18379009HCID 18379009, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Example 20A (0.25 g, 0.95 mmol), cyclopropanecarboxaldehyde (71 mL, 0.95 mmol), and sodium cyanoborohydride (119 mg, 1.86 mmol), in methanol (3.5 mL) was heated to 50° C., stirred for 2 hours, cooled to room temperature, and treated with water. The resulting precipitate was collected by filtration, dried, and purified by flash column chromatography with 30% ethyl acetate/hexanes to provide the desired product.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customdried
  3. custompurified by flash column chromatography with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-9ca78e62925e4e7487ce3fd507302503
Source dataset
uspto-grants-2002_12
Patent number
US06495562B1

Reaction notes

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