Benzyl chloroformate → Benzyl 7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-ylcarbamate

HRID 1672541ノート

反応式

HRID 1672541 の反応式
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].CC[N:14]([CH:18]([CH3:20])[CH3:19])C(C)C.[OH-:21].[Na+]>C(Cl)Cl>[OH:21][CH:10]1[CH2:11][C:19]2[C:18]([NH:14][C:2](=[O:3])[O:4][CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:20][CH:5]=[CH:6][C:7]=2[CH2:8][CH2:9]1

参加物

5

反応物 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 81531Diisopropylethylamine

生成物 1

HCID 66696602Benzyl 7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-ylcarbamate収率 61%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of benzyl chloroformate (5.84 mL, 41.1 mmol) in 5 mL CH2Cl2 was added dropwise via addition funnel to Example 24A (3.05 g, 18.7 mmol) and Hunig's base (8.14 mL, 46.7 mmol) in dichloromethane (55 mL) at ambient temperature. After 18 hr IN (aq) NaOH solution (50 mL) was added and the reaction was stirred vigorously for 15 min. The separated organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was triturated with diethyl ether and the solid collected by suction filtration. The result was 3.37 g (61% yield) of the title compound as a brown solid. 1H NMR (300 MHz, DMSO-d6) δ 8.82 (s, 1H), 7.30-7.45 (m, 5H), 7.14 (m, 1H), 7.05 (t, 1H), 6.90 (m, 1H), 5.12, (s, 2H), 4.77 (d, 1H), 3.87 (m, 1H), 2.86 (m, 2H), 2.71 (m, 1H), 2.43 (m, 1H), 1.84 (m, 1H), 1.58 (m, 1H). MS (APCI+) m/z 298 (M+H)+.

後処理

  1. washThe separated organic layer was washed with brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was triturated with diethyl ether
  6. filtrationthe solid collected by suction filtration

出典と根拠

ORDレコード
ord-0df89bc867e24a40ac0ba7eb3451fc65
出典データセット
uspto-grants-2011_08
特許番号
US07998993B2

反応ノート

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