Acetic Acid → HCID 57701026, compound

HRID 1186298Notes

Reaction equation

HRID 1186298 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH:13]1[CH2:17][CH2:16][C:15](=O)[CH2:14]1)([O-:3])=[O:2].CC(O)=O.[CH2:23]([NH2:25])[CH3:24].Cl.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH2:23]([NH:25][CH:15]1[CH2:16][CH2:17][CH:13]([C:7]2[C:6]3[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[NH:9][CH:8]=2)[CH2:14]1)[CH3:24]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 11198Ethylamine hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 57701046HCID 57701046, compound

Product 1

HCID 57701026HCID 57701026, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 3-(5-nitro-1H-indol-3-yl)cyclopentanone (1.6 g, 6.55 mmol) in 1,2-dichloroethane (50 mL) was added AcOH (0.40 mL, 6.55 mmol), EtNH2.HCl (0.53 g, 6.55 mmol) and NaBH(OAc)3 (2.1 g, 9.83 mmol) and the mixture left to stir overnight at room temperature. The reaction mixture was extracted with 2N NaOH (10 mL) and washed with dichloromethane (2×10 mL). The dichloromethane layer was separated and evaporated. The crude material was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 1:9) to obtain the product as a yellow solid as a mixture of diastereomers (1.2 g, 67%). 1H-NMR (CDCl3) δ 1.10-1.16 (m, 6H), 1.45-1.92 (m, 10H), 1.96-2.13 (m, 3H), 2.13-2.36 (m, 3H), 2.50-2.58 (m, 1H), 2.65-2.76 (m, 4H), 3.28-3.43 (m, 3H), 3.49-3.60 (m, 1H), 7.11 (d, 1H, J=1.8 Hz), 7.15 (d, 1H, J=1.5 Hz), 7.35 (s, 1H), 7.38 (s, 1H), 8.08 (d, 1H, J=2.1 Hz), 8.11 (d, 1H, J=2.1 Hz), 8.32 (brs, 1H, NH), 8.41 (brs, 1H, NH), 8.61 (d, 1H, J=2.1 Hz), 8.63 (d, 1H, J=2.1 Hz); EI-MS (m/z, %) 273 (M+, 90).

Workup

  1. waitthe mixture left
  2. extractionThe reaction mixture was extracted with 2N NaOH (10 mL)
  3. washwashed with dichloromethane (2×10 mL)
  4. customThe dichloromethane layer was separated
  5. customevaporated
  6. customThe crude material was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 1:9)

Sources & evidence

ORD record
ord-4f8c3e582ae24fbbb63fc9bc6a4b31ac
Source dataset
uspto-grants-2014_03
Patent number
US08673909B2

Reaction notes

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