Hydrochloric Acid → HCID 69894613, compound

HRID 2307052Notes

Reaction equation

HRID 2307052 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[C@@H:10]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24][C@@H:11]3[N:12](C(OC(C)(C)C)=O)[C:13]=2[CH:14]=[CH:15][CH:16]=1.[ClH:36]>O1CCOCC1>[ClH:36].[ClH:36].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[C@@H:10]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24][C@@H:11]3[NH:12][C:13]=2[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69894749HCID 69894749, compound

Product 1

HCID 69894613HCID 69894613, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(5aS*,10bS*)-Di(tert-butyl) 10-(2-fluorophenyl)-1,2,4,5,5a,10b-hexahydroazepino[4,5-b]indole-3,6-dicarboxylate (0.094 g, 0.19 mmol) was dissolved in a 4.0 N solution of HCl in dioxane (4 mL) and stirred at room temperature for 26.5 hours. After the reaction mixture was concentrated in vacuo CH3OH was added and the solution was concentrated in vacuo and recrystallized from CH3OH/EtOAc to give 0.054 g (72%) of a white solid as the title compound: mp 248.0-256.7° C. 1H NMR (400 MHz, DMSO-d6) δ 9.19 (m, 1 H), 9.05 (m, 1 H), 7.51-7.43 (m, 2 H), 7.36-7.29 (m, 3 H), 7.03-6.98 (m, 2 H) 4.34-4.33 (m, 1 H), 3.85 (m, 1 H), 3.29 (m, 1 H), 3.06 (m, 1 H), 2.90 (m, 1 H), 2.69-2.67 (m, 1 H), 2.27 (m, 2 H), 1.67 (m, 1 H), 1.36-1.34 (m, 1 H); 13C NMR (100 MHz, DMSO-d6) δ 159.8, 157.3, 132.7, 130.8, 130.7, 130.2, 130.1, 128.6, 126.4, 126.2, 124.8, 124.7, 115.9, 115.7, 59.7, 44.8, 43.9, 41.7, 26.5, 25.7: IR (diffuse reflectance) 2954 (s), 2847 (s), 2817 (s,b), 2755 (s), 2726 (s,b), 2668 (s,b), 2651 (s,b), 2572 (s,b), 2538 (s), 2469 (s), 2350, 2342, 1738, 1474, 771 cm−1; HRMS (FAB) calcd for C18H19FN2+H1: 283.1610 found 283.1612.

Workup

  1. concentrationAfter the reaction mixture was concentrated in vacuo CH3OH
  2. additionwas added
  3. concentrationthe solution was concentrated in vacuo
  4. customrecrystallized from CH3OH/EtOAc

Sources & evidence

ORD record
ord-7d36a252b39a49b1aea4224ea5e6a68d
Source dataset
uspto-grants-2004_12
Patent number
US06828314B2

Reaction notes

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