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Trifluoroacetic acid → HCID 57210991、化合物

HRID 1386798
ノート
印刷プレビュー

反応式

HRID 1386798 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:24])[CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])(C)C)=[O:18])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.N1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.[OH-].[Na+].ClC(OCC1C=CC=CC=1)=O>C(Cl)Cl.C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:24])[CH2:9][CH2:10][CH:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][CH2:20][C:23]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:18])[CH2:15][CH2:16]2)=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 6422Trifluoroacetic acidHCID 8082PiperidineHCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 22458227HCID 22458227、化合物

生成物 1

HCID 57210991HCID 57210991、化合物収率 95%

試薬・触媒・溶媒 2

HCID 6344
Dichloromethane
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 188 mg (0.56 mmol) of 4-(3-(4-fluorophenyl)-3-oxo-propyl)-1-(t-butoxycarbonyl) piperidine (from EXAMPLE 189, Step A) in 5 mL of CH2Cl2 at 0° C. was treated with 3 mL of TFA and the resulting mixture was stirred cold for 30 min. The solution was concentrated. A solution of the crude piperidine in 5 mL THF/5 mL of 1.0 N NaOH at 0° C. was treated with 0.09 mL (0.63 mmol) of benzyl chloroformate and the resulting mixture was stirred cold for 30 min. The reaction mixture was partitioned between 50 mL of ether and 10 mL of H2O and the layers were separated. The organic layer was washed with 10 mL of sat'd NaCl, dried and concentrated. Flash chromatography on 10 g of silica gel using 2:1 v/v hexanes/ether as the eluant afforded 196 mg (95%) of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.10-1.20 (m, 21), 1.43-1.53 (m, 1H), 1.60-1.71 (4H), 2.72-2.82 (m, 2H), 2.97 (t, J=7.5, 21), 4.154.21 (m, 2H), 5.12 (s, 2H), 7.11-7.15 (m, 2H), 7.26-7.36 (5H), 7.96-8.00 (m, 2H).

後処理

  1. concentrationThe solution was concentrated
  2. stirringthe resulting mixture was stirred cold for 30 min
  3. customThe reaction mixture was partitioned between 50 mL of ether and 10 mL of H2O
  4. customthe layers were separated
  5. washThe organic layer was washed with 10 mL of sat'd NaCl
  6. customdried
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-a3e9db2b4cff4202b38766b6871da238
出典データセット
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06265434B1

反応ノート

読み込み中…

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