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

HRID 1672541노트

반응식

HRID 1672541 반응식
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

참가 물질

5

반응물 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 81531Diisopropylethylamine

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-0df89bc867e24a40ac0ba7eb3451fc65
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998993B2

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