Sodium cyanoborohydride → 5-(3,4,5-Trimethoxyphenethyl)indoline

HRID 710291Notes

Reaction equation

HRID 710291 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[C:18]([O:22][CH3:23])[C:19]=1[O:20][CH3:21])[CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2.[BH3-]C#N.[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[C:18]([O:22][CH3:23])[C:19]=1[O:20][CH3:21])[CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH2:12][CH2:11]2

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 667264975-(3,4,5-Trimethoxyphenethyl)-1H-indole

Product 1

HCID 667266985-(3,4,5-Trimethoxyphenethyl)indolineYield 100.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Step B (0.12 g; 0.38 mmol) in tetrahydrofuran (THF)/acetic acid 1:1 mixture (6 ml) NaBH3CN (0.1 g; 1.16 mmol) was added at room temperature. After stirring for 1 h the solvents were removed in vacuo and the residue was diluted to 15 ml with Et2O and washed with 1 N NaOH (5 ml), H2O (2×5 ml), brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure to give the title compound (0.12 g; 100%), which was used in next step without further purification. 1H-NMR (CDCl3) 2.85 (s, 4H); 2.99 (tr, 2H, J=8.3 Hz); 3.52 (tr, 2H, J=8.3 Hz); 3.66 (broad s, 1H); 3.8 (s, 9H); 6.39 (s, 2H); 6.57 (d, 1H, J=7.9 Hz); 6.84 (d, 1H, J=7.9 Hz); 6.96 (s, 1H).

Workup

  1. customwere removed in vacuo
  2. additionthe residue was diluted to 15 ml with Et2O
  3. washwashed with 1 N NaOH (5 ml), H2O (2×5 ml), brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-81e869b117b64c55af58183d13a02376
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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