Sodium triacetoxyborohydride → HCID 57671260, compound

HRID 731379Notes

Reaction equation

HRID 731379 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH2:10][CH2:9][CH2:8][C:7]=1[NH:11][CH:12]([CH3:14])[CH3:13])=[O:5])[CH3:2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[NH:11][CH:12]([CH3:13])[CH3:14])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 57671255HCID 57671255, compound

Product 1

HCID 57671260HCID 57671260, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

2-Isopropylamino-cyclopent-1-enecarboxylic acid ethyl ester (2.44 g, 12.38 mmol) was dissolved in glacial acetic acid (30 mL) and sodium triacetoxyborohydride (7.87 g, 37.13 mmol) was added at 0° C. The solution was allowed to warm to 25° C. and stirred for 3 h. The acetic acid was removed in vacuo and the residue was dissolved in dichloromethane. The solution was washed with saturated aqueous sodium bicarbonate solution followed by saturated aqueous brine solution. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford the desired product, 2-isopropylamino-cyclopentanecarboxylic acid ethyl ester (1.5 g, 7.53 mmol, 60.8%), as a yellowish oil. LC-MS (ESI) calcd for C11H21NO2 199.16, found 200.2 [M+H+].

Workup

  1. customThe acetic acid was removed in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washThe solution was washed with saturated aqueous sodium bicarbonate solution
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c35ab577e15e49f780874c5fec451455
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

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