4-Fluorobenzylamine → HCID 59512587, compound

HRID 1158130Notes

Reaction equation

HRID 1158130 reaction equation
[F:1][C:2]1[C:29]([CH3:30])=[CH:28][C:5]([CH2:6][C@@H:7]([C:13]([N:15]2[C@H:19]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:18][O:17][C:16]2=[O:27])=[O:14])[CH2:8][CH2:9][CH2:10][CH:11]=O)=[CH:4][C:3]=1[CH3:31].[F:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37][NH2:38])=[CH:35][CH:34]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C>[F:1][C:2]1[C:29]([CH3:30])=[CH:28][C:5]([CH2:6][C@H:7]([CH2:8][CH2:9][CH2:10][CH2:11][NH:38][CH2:37][C:36]2[CH:39]=[CH:40][C:33]([F:32])=[CH:34][CH:35]=2)[C:13]([N:15]2[C@H:19]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:18][O:17][C:16]2=[O:27])=[O:14])=[CH:4][C:3]=1[CH3:31]

Participants

5

Reactant 3

HCID 673264-FluorobenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 59512602HCID 59512602, compound

Product 1

HCID 59512587HCID 59512587, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of (S)-5-(4-fluoro-3,5-dimethylbenzyl)-6-((R)-4-benzyl-2-oxooxazolidin-3-yl)-6-oxohexanal (0.039 g, 0.0917 mmol) and 4-fluorobenzyl amine (0.014 g, 0.110 mmol) in 3 mL of dichloroethane, was added NaBH(OAc)3 (0.027 g, 0.128 mmol). After stirring at room temperature for overnight, the reaction was quenched with 20 mL of saturated NaHCO3 solution and the reaction mixture was extracted with ethyl acetate (20 mL×3). The combined organic extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure. The product was isolated by Flash column chromatography (silica gel column) eluting with 0-10% methanol/dichloromethane to give the title compound as light yellow oil (0.030 g, 62% yield). LC-MS: tR=6.9 min; m/z 535 (M+H)+.

Workup

  1. customthe reaction was quenched with 20 mL of saturated NaHCO3 solution
  2. extractionthe reaction mixture was extracted with ethyl acetate (20 mL×3)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe product was isolated by Flash column chromatography (silica gel column)
  7. washeluting with 0-10% methanol/dichloromethane

Sources & evidence

ORD record
ord-3141cba112e64469a2d75bf9ebd75755
Source dataset
uspto-grants-2010_10
Patent number
US07807720B2

Reaction notes

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