Potassium bis(trimethylsilyl)amide → [2S,3S]-1-tert-butoxycarbonyl-2-phenyl-3-[(5-bromobenzofuran-7-yl)methyloxy]piperidine

HRID 1602927ノート

反応式

HRID 1602927 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH2:21][C@H:20]([OH:24])[C@@H:19]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].[Br:31][C:32]1[CH:33]=[C:34]([CH2:41]Br)[C:35]2[O:39][CH:38]=[CH:37][C:36]=2[CH:40]=1>COCCOC.O>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH2:21][C@H:20]([O:24][CH2:41][C:34]2[C:35]3[O:39][CH:38]=[CH:37][C:36]=3[CH:40]=[C:32]([Br:31])[CH:33]=2)[C@@H:19]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

参加物

6

反応物 3

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 10901890(2S,3S)-1-t-Butyloxycarbonyl-3-hydroxy-2-phenylpiperidineHCID 196085405-Bromo-7-bromomethylbenzofuran

生成物 1

HCID 57239557[2S,3S]-1-tert-butoxycarbonyl-2-phenyl-3-[(5-bromobenzofuran-7-yl)methyloxy]piperidine収率 48.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

Potassium bis(trimethylsilyl)amide (300 mg) was added to a stirred solution of [2S,3S]-N-tert-butoxycarbonyl-2-phenylpiperidine-3-ol (160 mg) in dry 1,2-dimethoxyethane (3.0 ml) under a dry nitrogen atmosphere. After 30 minutes 5-bromo-7-bromomethylbenzofuran (290 mg) was added, and the reaction stirred for 18 hours at room temperature. The resulting mixture was then diluted with water (50 ml), and extracted into ethyl acetate (2×50 ml). The organic layers were separated and washed with brine (20 ml), dried over MgSO4, filtered and the solvent removed under reduced pressure. Purification by MPLC (20% ethyl acetate/n-hexane), afforded [2S,3S]-1-tert-butoxycarbonyl-2-phenyl-3-[(5-bromobenzofuran-7-yl)methyloxy]piperidine as a yellow gum (136 mg). 1H NMR (360 MHz,CDCl3)δ1.43 (9H, s), 1.65 (2H, m), 1.92 (2H, m), 2.70 (1H, t d, J=7.2, 3.0 Hz), 3.74 (2H,m), 4.90 (2H, d, J=5.0 Hz), 5.74 (1H, br s), 6.71 (1H, d, J=1.0 Hz), 7.30-7.42 (4H, m), 7.58 (3H, m), 7.75 (1H, d, J=1.0 Hz); MS m/z CI+ 487 (M+H+).

後処理

  1. extractionextracted into ethyl acetate (2×50 ml)
  2. customThe organic layers were separated
  3. washwashed with brine (20 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customPurification by MPLC (20% ethyl acetate/n-hexane)

出典と根拠

ORDレコード
ord-1ac02ae861834e52a5602f453c461099
出典データセット
uspto-grants-1999_11
特許番号
US05985896

反応ノート

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