Sodium Bicarbonate → HCID 68872593, compound

HRID 660029Notes

Reaction equation

HRID 660029 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[Cl:14])[N:10]([CH2:15][CH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1)[CH:9]=[CH:8]2)=O.[H-].C([Al+]CC(C)C)C(C)C.C([O-])(O)=O.[Na+].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl.CO>[C:27]([O:26][C:24]([N:21]1[CH2:22][CH2:23][CH:18]([CH2:17][CH2:16][CH2:15][N:10]2[C:11]3[C:7](=[CH:6][C:5]([CH2:3][OH:2])=[C:13]([Cl:14])[CH:12]=3)[CH:8]=[CH:9]2)[CH2:19][CH2:20]1)=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 9855836Potassium sodium tartarateHCID 21225700Diisobutylaluminumhydride2×HCID 68934605HCID 68934605, compound

Product 1

HCID 68872593HCID 68872593, compoundYield 53.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

To a 0° C. solution of 1-[3-(1-tert-butoxycarbonyl-piperidin-4-yl)-propyl]-6-chloro-1H-indole-5-carboxylic acid methyl ester (1.10 g, 2.53 mmol) in toluene (20 mL) was added diisobutylaluminum hydride (1 M in hexanes; 5.06 mL, 5.06 mmol) dropwise. The mixture was stirred for 1 h. Additional diisobutylaluminum hydride (1 M in hexanes; 5.06 mL, 5.06 mmol) was added. After 1 h, the mixture was diluted at rt with satd. aq. NaHCO3 (2 mL), MeOH (5 mL), CHCl3 (10 mL), and satd. aq. sodium potassium tartrate (10 mL). The mixture was stirred vigourously until the layers separated. The organic layer was dried and concentrated to give the crude product (117 mg), which was purified by FCC (EtOAc/hexanes) to give 550 mg (27%) of a white solid. 1H NMR (400 MHz, CDCl3): 7.65 (s, 1H), 7.34 (s, 1H), 7.07 (d, J=3.1, 1H), 6.45 (d, J=3.1, 1H), 4.85-4.80 (m, 2H), 4.04 (t, J=7.1, 2H), 2.69-2.55 (m, 2H), 2.30-2.21 (m, 2H), 1.85-1.76 (m, 2H), 1.62-1.54 (m, 2H), 1.44 (s, 9H), 1.40-1.18 (m, 3H), 1.03 (dq, J=12.6, 4.4, 2H).

Workup

  1. waitAfter 1 h
  2. additionthe mixture was diluted at rt with satd
  3. stirringThe mixture was stirred vigourously until the layers
  4. customseparated
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customto give the crude product (117 mg), which
  8. customwas purified by FCC (EtOAc/hexanes)

Sources & evidence

ORD record
ord-dcc0276bb2c04e0aa137af1596a4fc64
Source dataset
uspto-grants-2011_12
Patent number
US08084466B2

Reaction notes

Loading…