Water → HCID 131736724, compound

HRID 1483839Notes

Reaction equation

HRID 1483839 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][C@H:4]([C:7](O)=O)[CH2:3]1.[C:10]([O-:13])([O-])=O.[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH2:24]>CC#N>[CH2:16]([N:1]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@H:2]1[CH2:6][CH2:5][C@H:4]([C:7]([O:13][CH2:10][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:24])[CH2:3]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 656716(1S,3S)-3-Aminocyclopentanecarboxylic acid

Product 1

HCID 131736724HCID 131736724, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
80 °C

Procedure

To a 80° C. mixture of trans-3-aminocyclopentanecarboxylic acid (1 g, 7.74 mmol) and K2CO3 (3.2 g, 23.22 mmol) in CH3CN (20 mL) was added dropwise a solution of benzyl bromide (3.2 mL, 27.1 mmol) in CH3CN (10 mL). The mixture was heated at 80° C. overnight. The mixture was cooled and poured into water (150 mL) and extracted with EtOAc (100 mL*3). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by combi flash to give trans-benzyl 3-(dibenzylamino)cyclopentanecarboxylate (2.8 g, 90.6%) as a white solid.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with EtOAc (100 mL*3)
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by combi flash

Sources & evidence

ORD record
ord-51e2c1d478594b589f28b4054934ba5b
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

Loading…