Dimethylamine → HCID 69945382, compound

HRID 1358479Notes

Reaction equation

HRID 1358479 reaction equation
[CH:1]([N:4](C(C)C)[CH2:5]C)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CNC.[CH:40]1[C:52]2[CH:51]([CH2:53][O:54][C:55]([N:57]3[CH2:66][CH2:65][C:64]4[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=4)[C@H:58]3[C:67]([OH:69])=O)=[O:56])[C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[C:44]=2[CH:43]=[CH:42][CH:41]=1>C(O)C.C(Cl)Cl.O.C(Cl)Cl>[CH3:1][N:4]([CH3:5])[C:67]([C@@H:58]1[C:59]2[C:64](=[CH:63][CH:62]=[CH:61][CH:60]=2)[CH2:65][CH2:66][N:57]1[C:55]([O:54][CH2:53][CH:51]1[C:52]2[CH:40]=[CH:41][CH:42]=[CH:43][C:44]=2[C:45]2[C:50]1=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:56])=[O:69]

Participants

8

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 11258057(1S)-2-{[(9H-Fluoren-9-yl)methoxy]carbonyl}-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

Product 1

HCID 69945382HCID 69945382, compoundYield 84.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 21908982Water methylene chlorideSolvent

Procedure

1.61 g of diisopropylethylamine, 5.53 g of BOP and then 5 ml of a 5.6M solution of dimethylamine in ethanol are added to a solution of 5 g of (1S)-2-(9-fluorenylmethoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (commercial) in 100 ml of DCM and the mixture is left stirring for 3 hours at AT. The reaction mixture is taken up in a water/DCM mixture, after separation by settling the organic phase is washed with a 5% KHSO4 solution and dried over Na2SO4, and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, elution being carried out with a DCM/AcOEt (70/30, v/v) mixture. 4.5 g of the expected product are obtained in the form of an oil.

Workup

  1. waitthe mixture is left
  2. customafter separation
  3. washis washed with a 5% KHSO4 solution
  4. dry with materialdried over Na2SO4
  5. customthe solvent is evaporated under vacuum
  6. customThe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-12348984bd1f490cbe614915f739ece6
Source dataset
uspto-grants-2003_07
Patent number
US06596732B2

Reaction notes

Loading…