Tetrahydrofuran → HCID 66936453, compound

HRID 1028206Notes

Reaction equation

HRID 1028206 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)C(O)=O.C1C=CC(P([N:27]=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.[NH2:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[CH2:37][N:36]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:35][CH2:34]2.[O:48]1[CH2:52]CCC1>C(N(CC)CC)C>[C:44]([O:43][C:41]([N:36]1[CH2:35][CH2:34][C:33]2[C:38](=[CH:39][CH:40]=[C:31]([NH:30][C:52]([NH:27][C:6]3[CH:10]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[O:11][CH3:12])=[O:48])[CH:32]=2)[CH2:37]1)=[O:42])([CH3:47])([CH3:46])[CH3:45]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 199401P,P-Diphenylphosphinic azideHCID 27373645-Fluoro-2-methoxybenzoic acidHCID 27563716-Amino-2-N-Boc-1,2,3,4-tetrahydro-isoquinoline

Product 1

HCID 66936453HCID 66936453, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A tetrahydrofuran (20 mL) solution of 5-fluoro-2-methoxybenzoic acid (1.00 g), DPPA (1.25 mL), and triethylamine (1.6 mL) was heated to reflux for 1 hour. A tetrahydrofuran (10 mL) solution of 6-amino-2N-Boc-1,2,3,4-tetrahydroisoquinoline (1.00 g) was added to the reaction solution. The reaction mixture was further heated to reflux for 5.5 hours, then cooled to room temperature, and then concentrated. The residue was purified by chromatography (dichloromethane/ethyl acetate=20:1→4:1) to obtain the title compound (1.51 g, 90%) as a white solid.

Workup

  1. temperatureto reflux for 1 hour
  2. temperatureThe reaction mixture was further heated
  3. temperatureto reflux for 5.5 hours
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography (dichloromethane/ethyl acetate=20:1→4:1)

Sources & evidence

ORD record
ord-a389558280ad4ee88fe89e425fbfa799
Source dataset
uspto-grants-2014_05
Patent number
US08735425B2

Reaction notes

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