1H-Indole-6-carboxaldehyde → Indole

HRID 14325

Reaction equation

HRID 14325 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](C=O)[CH:8]=2)[CH:3]=[CH:2]1.C(O)(=O)C.NC[C@@H](O)[C@@H](NC(=O)OC(C)(C)C)CC1C=C(F)C=C(F)C=1.[BH4-].[Na+]>CC(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 27734351H-Indole-6-carboxaldehydeHCID 4311764Sodium borohydrideHCID 86594203HCID 86594203, compound

Product 1

HCID 798IndoleYield 62.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred solution of 1H-indole-6-carbaldehyde (99 mg, 0.68 mmol) and tert-butyl (1S,2R)-3-amino-1-(3,5-difluorobenzyl)-2-hydroxypropylcarbamate acetate 3 (256 mg, 0.68 mmol) in 2-propanol (3 mL) was added sodium borohydride (30 mg, 0.82 mmol). The reaction mixture was stirred for 12 h., quenched with methanol, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:1 ethyl acetate/hexanes) provided indole (50 mg): 1H NMR (300 MHz, CDCl3) δ 8.41 (br s, 1H), 7.60 (d, J=8 Hz, 1H), 7.38 (s, 1H), 7.21 (t, J=3 Hz, 1H), 7.04 (dd, J=8, 1 Hz, 1H), 6.71-6.73 (m, 3H), 6.61-6.68 (m, 1H), 6.53 (s, 1H), 5.38 (br s, 2H), 4.66 (d, J=9 Hz, 1H), 3.89 (s, 2H), 3.49-3.54 (m, 1H), 2.91-2.98 (m, 1H), 2.62-2.73 (m, 3H), 1.35 (s, 9H).

Workup

  1. customquenched with methanol
  2. concentrationconcentrated under reduced pressure
  3. customPurification by flash column chromatography (silica, 1:1 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b5d89e8898184893be2e9ad5c582c649
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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