1H-Indole-6-carboxaldehyde → Indole

HRID 14325

반응식

HRID 14325 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 798Indole수율 62.8%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-b5d89e8898184893be2e9ad5c582c649
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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