Acetic Acid → HCID 68746626, compound

HRID 1864790Notes

Reaction equation

HRID 1864790 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[C:19]([O:23][C:24]([N:26]1[CH2:32][CH2:31][CH2:30][C@H:27]1[CH:28]=O)=[O:25])([CH3:22])([CH3:21])[CH3:20].[F:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH2:39])=[CH:36][CH:35]=1>ClCCCl.ClCCl>[C:19]([O:23][C:24]([N:26]1[CH2:32][CH2:31][CH2:30][C@@H:27]1[CH2:28][NH:39][CH2:38][C:37]1[CH:40]=[CH:41][C:34]([F:33])=[CH:35][CH:36]=1)=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 673264-FluorobenzylamineHCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 68746626HCID 68746626, compoundYield 77.8%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (15.9 g, 75.4 mmol) and enough acetic acid to bring the pH to 5 were added to a solution of N-tert-butoxycarbonyl-L-prolinal (5 g, 25 mmol) and 4-fluorobenzylamine (6.28 g, 50.3 mmol) in 200 mL of 1,2-dichloroethane. The mixture was stirred at ambient temperature overnight, and then it was diluted with dichloromethane, and washed with saturated sodium bicarbonate solution. The organic phase was dried over magnesium sulfate, filtered and concentrated to leave the crude product. Chromatography (elution with methanol/ethyl acetate) afforded 6.0 g of product.

Workup

  1. washwashed with saturated sodium bicarbonate solution
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto leave the crude product
  6. washChromatography (elution with methanol/ethyl acetate)

Sources & evidence

ORD record
ord-6dfdd5dabb884f2d96abeec53f5a4707
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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