Benzaldehyde → HCID 67549475, compound

HRID 490586Notes

Reaction equation

HRID 490586 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].[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CC(O)=O>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([NH:10][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[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 240BenzaldehydeHCID 49130641-Tert-butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67549475HCID 67549475, 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, dissolved in DCM and cooled to 0 centigrade is added a corresponding benzaldehyde, then NaBH(OAc)3 and 5 drops of HOAc. The mixture is warmed to room temperature and stirred overnight. The mixture is diluted with DCM, washed with brine, and dried. After removal of solvent, the crude 4-(benzylamino)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester is obtained (33) and used for the next step without further purification.

Workup

  1. temperaturecooled to 0 centigrade
  2. washwashed with brine
  3. customdried
  4. customAfter removal of solvent

Sources & evidence

ORD record
ord-ddadc9e4ae78492b9bb1be84d3b3ce8d
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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