Sodium Hydroxide → HCID 10158265, compound

HRID 966541Notes

Reaction equation

HRID 966541 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH:21]([CH3:25])[C:22](=O)[CH3:23])[CH:18]=2)[NH:13][C:12]=1[CH3:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClC(Cl)C>[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH:21]([CH3:25])[CH:22]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH3:23])[CH:18]=2)[NH:13][C:12]=1[CH3:26])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 23393849HCID 23393849, compound

Product 1

HCID 10158265HCID 10158265, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

2-Methyl-5-(1-methyl-2-oxo-propoxy)-1H-indole-3-carboxylic acid benzyl ester (0.248 g, 0.707 mmol) and pyrrolidine (0.05 g, 0.706 mmol) were mixed together in dichloroethane and stirred under N2 at room temperature for 1 hour. The reaction was then cooled to 0° C. whereupon sodium triacetoxyborohydride (0.209 g, 0.988 mmol) was added. After 30 minutes, the reaction was then permitted to warm to rt and stirred for a further 2 hours. It was then stopped by the addition of 1N NaOH (10 mL). The mixture was then extracted with EtOAc and the combined organic layers washed with brine and dried over anhydrous Na2SO4 Purification on SiO2 (10% MeOH/CH2Cl2) gave 0.110 g (38%) of the desired compound, mp 94-98° C. 1HNMR (400 MHz, DMSO): 1.58 (d, J=6.10 Hz, 3H), 1.60 (b, 4H), 2.40 (b, 4H), 2.59 (s, 3H, ArCH3),3.35 (b, 1H), 4.43 (m, 1H), 5.26 (s, 2H), 6.69 (d, J=8.44 Hz, 1H), 7.19 (d, J=8.64 Hz, 1H), 7.28-7.44 (m, 6H), 11.72 (s, H, H). MS APCI+) m/z 407.2(MH+). Anal. Calcd for C25H30N2O3.0.20H2O: C, 3.21;H,7.47; N, 6.83. Found: C, 72.84: H, 7.57: N, 6.56 I (KBr): 3294, 2973, 1691, 1665, 1454, 1167, 1073 cm−1.

Workup

  1. additionwas added
  2. waitAfter 30 minutes
  3. temperatureto warm to rt
  4. stirringstirred for a further 2 hours
  5. extractionThe mixture was then extracted with EtOAc
  6. washthe combined organic layers washed with brine
  7. dry with materialdried over anhydrous Na2SO4 Purification on SiO2 (10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-3588461edbff4056b60a01442417438c
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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