1,2-Ethanediamine, N1,N1-dimethyl-N2-(phenylmethyl)- → 3-[Benzyl-(2-dimethylamino-ethyl)-carbamoyl]-3,4-dihydro-1h-isoquinoline-2-carboxylic acid tert-butyl ester

HRID 268607Notes

Reaction equation

HRID 268607 reaction equation
[CH3:1][C:2]([O:5][C:6]([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:7])([CH3:4])[CH3:3].CN(C(F)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:36]([NH:43][CH2:44][CH2:45][N:46]([CH3:48])[CH3:47])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>ClCCl>[C:2]([O:5][C:6]([N:8]1[CH:17]([C:18](=[O:20])[N:43]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:44][CH2:45][N:46]([CH3:48])[CH3:47])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 660291,2-Ethanediamine, N1,N1-dimethyl-N2-(phenylmethyl)-HCID 664088(3S)-2-((tert-butoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidHCID 2774761Tetramethylfluoroformamidinium hexafluorophosphate

Product 1

HCID 210623603-[Benzyl-(2-dimethylamino-ethyl)-carbamoyl]-3,4-dihydro-1h-isoquinoline-2-carboxylic acid tert-butyl esterYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-Boc-L-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (2.0 g, 7.2 mmole) in dichloromethane (20 mL) was added TFFH (1.91 g, 7.2 mmole). The mixture was cooled to 0° C. and N′-benzyl-N,N-dimethylethylenediamine (2.57 g, 14.4 mmole) was added to the reaction. The reaction was allowed to warm to room temperature and stirred for 6 h. The reaction was then quenched with water (20 mL), and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The organic residue was purified by flash chromatography on silica gel, eluting with dichloromethane/2.0 M ammonia in ethyl alcohol (96:4) to give 1d (0.81 g, 26%) as a pale yellow oil.

Workup

  1. temperatureto warm to room temperature
  2. customThe reaction was then quenched with water (20 mL)
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe organic residue was purified by flash chromatography on silica gel
  7. washeluting with dichloromethane/2.0 M ammonia in ethyl alcohol (96:4)

Sources & evidence

ORD record
ord-6a8e00c363c7450bb99b112217215624
Source dataset
uspto-grants-2008_11
Patent number
US07446115B2

Reaction notes

Loading…