Cyclopentylamine → HCID 86729453, compound

HRID 1507048Notes

Reaction equation

HRID 1507048 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=O.[CH:14]1([NH2:19])[CH2:18][CH2:17][CH2:16][CH2:15]1.[BH4-].[Na+]>CO>[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH2:9][NH:19][CH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 27740493-(oxiran-2-ylmethoxy)benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 86729453HCID 86729453, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(oxiran-2-ylmethoxy)benzaldehyde (1.0 g, 5.61 mmol) in MeOH (15 mL) was added cyclopentanamine (502 mg, 5.89 mmol) at room temperature. After 4 h, sodium borohydride (318 mg, 8.42 mmol) was added in portions and the mixture was stirred for another 1 h. The reaction mixture was quenched by adding aqueous 1 N HCl until the pH was adjusted to 4-5. The resulting solution was diluted with ethyl acetate, washed with water, dried over sodium sulfate, filtered and concentrated. The crude product was used in the next step without further purification. (1.1 g, yield 79%) MS (ESI+) e/z: 248.2 [M+1]+.

Workup

  1. customThe reaction mixture was quenched
  2. additionby adding aqueous 1 N HCl until the pH
  3. additionThe resulting solution was diluted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-1af4170858c64dd39e96ace5e235c612
Source dataset
uspto-grants-2015_12
Patent number
US09221794B2

Reaction notes

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