Dimethylamine → HCID 69944225, compound

HRID 1358478Notes

Reaction equation

HRID 1358478 reaction equation
C(OC([N:8]1[C@H:17]([C:18]([OH:20])=O)[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.[CH2:21]([N:23](CC)[CH2:24]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.C(Cl)[Cl:59]>>[ClH:59].[CH3:21][N:23]([CH3:24])[C:18]([C@@H:17]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][NH:8]1)=[O:20]

Participants

6

Reactant 5

HCID 674DimethylamineHCID 6344DichloromethaneHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 664088(3S)-2-((tert-butoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Product 1

HCID 69944225HCID 69944225, compound

Procedure

A solution of 5 g of (3S)-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (commercial) in 50 ml of DCM is cooled to 0° C. and 5.45 g of triethylamine and then 8 g of BOP are added. Dimethylamine gas is then added by sparging for 5 minutes and the mixture is left stirring for 18 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 with a 5% Na2CO3 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 g of the expected product are obtained in the form of an oil, which crystallizes.

Workup

  1. customby sparging for 5 minutes
  2. waitthe mixture is left
  3. customafter separation
  4. washis washed with a 5% KHSO4 solution and with a 5% Na2CO3 solution
  5. dry with materialdried over Na2SO4
  6. customthe solvent is evaporated under vacuum
  7. customThe residue is chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-660b5b2859a74399b521e8a013559e3b
Source dataset
uspto-grants-2003_07
Patent number
US06596732B2

Reaction notes

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