Dimethylamine → Phenylmethyl (2S,4R)-2-[(dimethylamino)carbonyl]-4-hydroxy-1-pyrrolidinecarboxylate

HRID 1581713Notes

Reaction equation

HRID 1581713 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:12]1[C:17]([OH:19])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.C1CC[CH:33]([N:36]=[C:37]=NC2CCCCC2)CC1.CNC>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:12]1[C:17]([N:36]([CH3:37])[CH3:33])=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 3915171-(Phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Product 1

HCID 16123358Phenylmethyl (2S,4R)-2-[(dimethylamino)carbonyl]-4-hydroxy-1-pyrrolidinecarboxylateYield 78.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 15 g of (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxy-2-pyrrolidinecarboxylic acid, 7.64 g of HOBT and 11.65 g of DCC in 250 ml of DCM is stirred for 1 hour at RT. The reaction mixture is cooled on an ice bath, dimethylamine gas is added by sparging for 10 minutes and this mixture is stirred for 3 hours at RT. An insoluble material is filtered off and the filtrate is concentrated under vacuum. The residue is taken up in saturated Na2CO3 solution and extracted with DCM, the organic phase is dried over Na2SO4 and the solvent is evaporated off under vacuum. 13 g of the expected product are obtained in the form of an oil.

Workup

  1. temperatureThe reaction mixture is cooled on an ice bath
  2. customby sparging for 10 minutes
  3. stirringthis mixture is stirred for 3 hours at RT
  4. filtrationAn insoluble material is filtered off
  5. concentrationthe filtrate is concentrated under vacuum
  6. extractionextracted with DCM
  7. dry with materialthe organic phase is dried over Na2SO4
  8. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-bd5c175ef4a047df8f9d4d9cb951712c
Source dataset
uspto-grants-2004_05
Patent number
US06730695B2

Reaction notes

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