(1,1'-Biphenyl)-2-carboxaldehyde → HCID 89527718, compound

HRID 1778574Notes

Reaction equation

HRID 1778574 reaction equation
[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:2](C=O)=[CH:3][CH:4]=[CH:5][CH:6]=1.[NH2:15][C@H:16]1[CH2:20][CH2:19][C@@H:18]([C:21]([OH:23])=[O:22])[CH2:17]1.[C:24](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.C(O)(=O)C.[Cl-].[Na+]>[C:12]1([CH2:24][NH:15][C@H:16]2[CH2:20][CH2:19][C@@H:18]([C:21]([OH:23])=[O:22])[CH2:17]2)[CH:11]=[CH:10][C:9]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 121052(1,1'-Biphenyl)-2-carboxaldehydeHCID 150203549805-32-5HCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 89527718HCID 89527718, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 5234Sodium ChlorideSolvent

Procedure

Biphenyl carboxaldehyde (2.82 g, 15.5 mmol) was added to a stirred solution of (1R,3S)-3-aminocyclopentanecarboxylic acid (2.0 g, 15.5 mmol) in anhydrous methanol (50 mL) and acetic acid (2 mL). After stirring at room temperature for 1 hour, sodium triacetoxyborohydride (6.57 g, 31 mmol) was added portion wise over 10 minutes and the reaction was stirred at room temperature for 4 hours, diluted with saturated aqueous sodium chloride, and extracted with ethyl acetate (3×30 mL). The combined organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give crude (1R,3S)-3-(biphen-4-ylmethyl-amino)-cyclopentane carboxylic acid, which was used in the next step without further purification; m/z for C19H21NO2 expected 295.2. found 318.1 (M+Na)+, 296.3 (M+H)+.

Workup

  1. stirringthe reaction was stirred at room temperature for 4 hours
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. washThe combined organic phase was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4ecada57c044c4eb97c532a0242c160
Source dataset
uspto-grants-2016_02
Patent number
US09266908B2

Reaction notes

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