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2,2,2-Trifluoroethyl formate → methyl(7R)-14-cyclohexyl-7-{methyl[2-(methylamino)ethyl]amino}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

HRID 421945
Notes
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Reaction equation

HRID 421945 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([CH3:34])[C@@H:5]1[CH2:12][N:11]2[C:13]3[CH:14]=[C:15]([C:26]([O:28][CH3:29])=[O:27])[CH:16]=[CH:17][C:18]=3[C:19]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[C:10]2[C:9]2[CH:30]=[CH:31][CH:32]=[CH:33][C:8]=2[O:7][CH2:6]1.[CH:35](OCC(F)(F)F)=O>C1COCC1>[CH:20]1([C:19]2[C:18]3[CH:17]=[CH:16][C:15]([C:26]([O:28][CH3:29])=[O:27])=[CH:14][C:13]=3[N:11]3[C:10]=2[C:9]2[CH:30]=[CH:31][CH:32]=[CH:33][C:8]=2[O:7][CH2:6][C@H:5]([N:4]([CH3:34])[CH2:3][CH2:2][NH:1][CH3:35])[CH2:12]3)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 1416812,2,2-Trifluoroethyl formateHCID 66674669methyl(7R)-7-[(2-aminoethyl)(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Product 1

HCID 66675300methyl(7R)-14-cyclohexyl-7-{methyl[2-(methylamino)ethyl]amino}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylateYield 40%

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent

Procedure

A solution (0.1 M) of methyl(7R)-7-[(2-aminoethyl)(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate in THF was treated dropwise with 2,2,2-trifluoroethyl formate (1.5 eq.) and stirred overnight at RT. The volatiles were removed in vacuo and the residue dissolved (0.1 M) in THF and treated dropwise with BH3-DMS complex (2M in THF; 5 eq.). The resulting solution was stirred at RT for 3 h. The reaction was quenched by the careful addition of HCl/MeOH (1.25 M) and the resulting solution heated to dryness. The residue was then partitioned between sat. aq. NaHCO3 and EtOAc. The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude was purified by FC (EtOAc/MeOH 99.5:0.5+1% NEt3) to afford the product (40%). (ES+) m/z 476 (M+H)+.

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe residue dissolved (0.1 M) in THF
  3. stirringThe resulting solution was stirred at RT for 3 h
  4. customThe reaction was quenched by the careful addition of HCl/MeOH (1.25 M)
  5. temperaturethe resulting solution heated to dryness
  6. customThe residue was then partitioned between sat. aq. NaHCO3 and EtOAc
  7. washThe combined organics were washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude was purified by FC (EtOAc/MeOH 99.5:0.5+1% NEt3)

Sources & evidence

ORD record
ord-7ee733c484ba419bb2ce3a58c5ce1203
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08101595B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes