2,4-Difluorobenzaldehyde → HCID 68862811, compound

HRID 490661Notes

Reaction equation

HRID 490661 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([NH2:10])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].[F:18][C:19]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:20]=1[CH:21]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CC(O)=O>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([NH:10][CH2:21][C:20]2[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:19]=2[F:18])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4]

Participants

6

Reactant 3

HCID 737702,4-DifluorobenzaldehydeHCID 49130641-Tert-butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 68862811HCID 68862811, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-amino-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (2 mmol, 1 equvi) was dissolved in dry DCM (20 ml) cooled to 0 centigrade was added 2,4-difluorobenzaldehyde (1.05 equiv), then NaBH(OAc)3 (2 equiv) and 5 drops of HOAc. The mixture was warmed to room temperature and stirred overnight. The mixture was diluted with DCM, washed with brine, and dried over anhydrous sodium sulfate. After removal of solvent, the crude product was used for the next step without further purification. MS m/e=371.4 [M+H]+.

Workup

  1. temperaturecooled to 0 centigrade
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter removal of solvent
  5. customthe crude product was used for the next step without further purification

Sources & evidence

ORD record
ord-67c577eb31d84c2aa7f0754f6ef30716
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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