HCID 67346293, compound → HCID 67344016, compound

HRID 1669445Notes

Reaction equation

HRID 1669445 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:36]([O:38][CH3:39])=[O:37])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17][CH:16]([CH2:26][CH2:27][N:28]([CH3:35])[C:29](=O)[CH2:30][CH2:31][NH:32][CH3:33])[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C1COCC1>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:36]([O:38][CH3:39])=[O:37])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17][CH:16]([CH2:26][CH2:27][N:28]([CH3:35])[CH2:29][CH2:30][CH2:31][NH:32][CH3:33])[CH2:15]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 1

HCID 67346293HCID 67346293, compound

Product 1

HCID 67344016HCID 67344016, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 14-cyclohexyl-7(R,S)-{2-[methyl(N-methyl-β-alanyl)amino]ethyl}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (0.02 M) in THF was treated dropwise with BH3-DMS complex (2M in THF; 10 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 refluxed for 2 h. The mixture was cooled before concentrating in vacuo. The crude material was purified by FC (EtOAc/MeOH/Et3N 90:8:2) affording the product as a yellow oil (48%, over steps 8, 9). (ES+) m/z 518 (M+H)+.

Workup

  1. customThe reaction was quenched by the careful addition of HCl/MeOH (1.25 M)
  2. temperaturethe resulting solution refluxed for 2 h
  3. temperatureThe mixture was cooled
  4. concentrationbefore concentrating in vacuo
  5. customThe crude material was purified by FC (EtOAc/MeOH/Et3N 90:8:2)

Sources & evidence

ORD record
ord-7ed4ce51548840afb85b9b1bf1864ed6
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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