Hydrochloric Acid → (R)-1-(6-azido-3,4,6,7,8,9-hexahydrobenzo[g]isoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone

HRID 1444699Notes

Reaction equation

HRID 1444699 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]3[CH2:18][CH2:17][CH2:16][C@H:15](O)[C:10]=3[CH:11]=2)[CH2:6]1)=[O:4].C1C=CC(P([N:36]=[N+:37]=[N-:38])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1.Cl>C1(C)C=CC=CC=1>[N:36]([C@H:15]1[C:10]2[CH:11]=[C:12]3[C:7](=[CH:8][C:9]=2[CH2:18][CH2:17][CH2:16]1)[CH2:6][N:5]([C:3](=[O:4])[C:2]([F:21])([F:20])[F:1])[CH2:14][CH2:13]3)=[N+:37]=[N-:38]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 86602828(S)-2,2,2-trifluoro-1-(6-hydroxy-3,4,6,7,8,9-hexahydrobenzo[g]isoquinolin-2(1H)-yl)ethanone

Product 1

HCID 58597252(R)-1-(6-azido-3,4,6,7,8,9-hexahydrobenzo[g]isoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (S)-2,2,2-trifluoro-1-(6-hydroxy-3,4,6,7,8,9-hexahydrobenzo[g]isoquinolin-2(1H)-yl)ethanone (3.0 g, 10 mmol) in 30 mL of toluene at −10° C. was added DPPA (2.6 mL, 12 mmol). To this stirred solution was then added DBU (1.8 mL, 12 mmol) dropwise while keeping the temperature below 0° C. After stirring at room temperature overnight, 7 mL of 10% HCl was added and the resulting solution was evaporated to dryness and directly submitted to flash chomatography (SiO2, hexane/EtOAc=100:10 to 100:15 to 100:20) to afford (R)-1-(6-azido-3,4,6,7,8,9-hexahydrobenzo[g]-isoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone as a colorless oil which was directly used in the next step.

Workup

  1. customthe temperature below 0° C
  2. customthe resulting solution was evaporated to dryness

Sources & evidence

ORD record
ord-ac7f942174e34f35bbf3cd44f310aadc
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

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