Sodium Hydroxide → HCID 10171440, compound

HRID 1789974Notes

Reaction equation

HRID 1789974 reaction equation
[CH3:1][N:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]3[C@@H:12]4[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14][C@@H:13]4[N:5]([C:6]=23)[CH2:4][CH2:3]1.[OH-].[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl.[Cl-].[Na+].O>[CH3:1][N:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]3[C@@H:12]4[CH2:18][CH2:17][NH:16][CH2:15][CH2:14][C@@H:13]4[N:5]([C:6]=23)[CH2:4][CH2:3]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 86591149HCID 86591149, compound

Product 1

HCID 10171440HCID 10171440, compoundYield 104.7%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Tert-butyl (6bS,11aS)-3-methyl-2,3,6b,7,8,10,11,11a-octahydro-1H,9H-azepino[4′,5′:4,5]pyrrolo[1,2,3-de]quinoxaline-9-carboxylate (115 mg, 0.33 mmol) was dissolved in 20% TFA (3 mL) in CH2Cl2 at rt. The reaction was stirred at rt for 2.5 hrs. Ice chips were added to the reaction, an then it was basified with 50% NaOH until pH=14. Brine (5 mL) was added and then the reaction was extracted with CH2Cl2 (2×10 mL). The combined organic layers were washed with brine, dried, and concentrated to afford the title compound (84.1 mg, 103%) as a viscous oil. 1H NMR (CDCl3, 300 MHz) δ 6.59–6.64 (1H, m), 6.48 (1H, d, J=7.3 Hz), 6.37 (1H, d, J=7.7 Hz), 3.4–3.7 (4H, m), 2.6–3.3 (10H, m), 1.7–2.2 (4H, m) ppm. MS (ESI): 244.2 (base, M+H)

Workup

  1. additionIce chips were added to the reaction
  2. extractionthe reaction was extracted with CH2Cl2 (2×10 mL)
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c2461e898ce941879538b46d3bf81bff
Source dataset
uspto-grants-2006_07
Patent number
US07071186B2

Reaction notes

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