Hydrochloric Acid → HCID 69659437, compound

HRID 1825720Notes

Reaction equation

HRID 1825720 reaction equation
O=[C:2]1[CH2:6][CH2:5][C@H:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[N:17])[CH:14]=3)[NH:9][CH:8]=2)[CH2:3]1.[CH3:18][NH:19][CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[CH3:18][N:19]([CH3:20])[CH:2]1[CH2:6][CH2:5][C@H:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[N:17])[CH:14]=3)[NH:9][CH:8]=2)[CH2:3]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 49836500HCID 49836500, compound

Product 1

HCID 69659437HCID 69659437, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

(1S)-3-(3-oxocyclopentyl)-1H-indole-5-carbonitrile (112 mg, 0.5 mMol) and dimethylamine (2.0 M solution in THF, 2.5 mL, 5.0 mMol) were dissolved in ethanol (2 mL). After stirring for 15 min, sodium triacetoxyborohydride (424 mg, 2.0 mMol) was added and the reaction continued for 2 h. The reaction was then diluted with water (5 mL) and made acidic (pH 3) with 6 M HCl. The reaction was then adjusted to pH 10 with sodium carbonate. It was extracted two times with ethyl acetate (50 mL) and the extracts were dried over sodium sulfate, concentrated in vacuo, and dried under high vacuum to give (1S)-3-(3-dimethylaminocyclopentyl)-1H-indole-5-carbonitrile (125 mg, 100%) as a cis/trans diastereomeric mixture. 1H NMR (500 MHz, d4-MeOH) δ 8.02 (0.7 H s), 7.99 (0.3 H, s), 7.46 (0.3 H, s), 7.44 (0.7 H, s), 7.35 (1 H, dd, J=8.24 1.53), 7.24 (0.7 H, s), 7.20 (0.3 H, s), 3.49 (0.3 H, m), 3.36 (0.7 H, m), 2.83 (0.2 H, m), 2.75 (0.8 H, m), 2.39 (1 H, m), 2.31 (6 H, s), 2.21 (1 H, m), 2.05 (1 H, m), 1.80 (2 H, m), 1.66 (1 H, m).

Workup

  1. waitthe reaction continued for 2 h
  2. extractionIt was extracted two times with ethyl acetate (50 mL)
  3. dry with materialthe extracts were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-fc1149b217cf4a7dadc61c08a366e255
Source dataset
uspto-grants-2006_05
Patent number
US07049314B2

Reaction notes

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