Acetic Acid → HCID 118308201, compound

HRID 1750488Notes

Reaction equation

HRID 1750488 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].[C:15]1(=O)[CH2:18][CH2:17][CH2:16]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl>[CH:15]1([NH:1][C@H:2]2[CH2:6][CH2:5][CH2:4][C@@H:3]2[NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 14496CyclobutanoneHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 17040218(1S,2S)-trans-N-Boc-1,2-cyclopentanediamine

Product 1

HCID 118308201HCID 118308201, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl N-[(1S,2S)-2-aminocyclopentyl]carbamate (CAS number 586961-34-4; 600 mg, 3.00 mmol) in dry DCM (10 ml) was added cyclobutanone (CAS number 1191-95-3; 248 μl, 3.30 mmol), acetic acid (257 μl, 4.49 mmol) and molecular sieves. The reaction was then stirred at room temperature for 1 hour. To this was then added sodium triacetoxyborohydride (952 mg, 4.49 mmol) and the reaction was allowed to stir at room temperature for 17 hours. The reaction was basified by the addition of 2M NaOH (aq) and the organics were extracted DCM, filtered through a hydrophobic frit and concentrated in vacuo.

Workup

  1. stirringto stir at room temperature for 17 hours
  2. extractionthe organics were extracted DCM
  3. filtrationfiltered through a hydrophobic frit
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-197ba219ad6841cca65852e7daed5452
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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