Diisobutylaluminum hydride → 1,1-Dimethylethyl 3-(3-oxopropyl)-1H-indole-1-carboxylate

HRID 1385914Notes

Reaction equation

HRID 1385914 reaction equation
[C:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][CH2:18][C:19](OC)=[O:20])=[CH:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[C:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][CH2:18][CH:19]=[O:20])=[CH:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 21716281tert-Butyl 3-(3-methoxy-3-oxopropyl)-1H-indole-1-carboxylate

Product 1

HCID 217162831,1-Dimethylethyl 3-(3-oxopropyl)-1H-indole-1-carboxylateYield 77.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of methyl 1-Boc-indole-3-propionate(2.0 g, 6.6 mmol) in toluene(20 ml) cooled at −78° C. was added a 1.5M toluene solution of DIBAL-H slowly so that the internal temperature was kept below −65° C. After addition, stirring was continued at −78° C. for additional 2 hrs. After quenched with 3 ml of MeOH, the mixture was poured into a NaCl solution and extrated with EtOAc. The combined organic solution was washed with a queous acid , NaHCO3 and bine, then dried over Na2SO4. Flush chromatography gave 1.4 g of oily product. 1H NMR(300 MHz, CDCl3) δ1.68(s, 9H), 2.84(t, 2H), 3.04(t, 2H), 7.20-7.40(m, 3H), 7.52(d, 1H), 8.14(d, 1H), 9.90(s, 1H); MS(ESI) Calc. for (M+1)+: 274. Found: 274.

Workup

  1. customwas kept below −65° C
  2. additionAfter addition
  3. customAfter quenched with 3 ml of MeOH
  4. additionthe mixture was poured into a NaCl solution
  5. washThe combined organic solution was washed with a queous acid , NaHCO3 and bine
  6. dry with materialdried over Na2SO4
  7. customFlush chromatography

Sources & evidence

ORD record
ord-999a2ce8cb7f493ab311c2d1352583f5
Source dataset
uspto-grants-2001_07
Patent number
US06265400B1

Reaction notes

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