Methanol → HCID 66673635, 화합물

HRID 426420노트

반응식

HRID 426420 반응식
[CH3:1][O:2][C:3](=[O:16])[C@@H:4]([CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[CH2:5][C:6](O)=[O:7].B.CO>O1CCCC1>[CH3:1][O:2][C:3](=[O:16])[C@@H:4]([CH2:9][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)[CH2:5][CH2:6][OH:7]

참가 물질

5

반응물 3

HCID 887MethanolHCID 6331BoraneHCID 22831490(S)-2-(Cyclohexylmethyl)succinic acid-1-methyl ester

생성물 1

HCID 66673635HCID 66673635, 화합물수율 70.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A mixture of (S)-2-cyclohexylmethyl-succinic acid 1-methyl ester (484 mg, 2.12 mmol) and tetrahydrofuran 10 mL) was stirred at room temperature and then cooled to 0° C. To the reaction mixture was added 1.0 M borane in tetrahydrofuran (4.2 mL) dropwise over 5 min. After 2 h, MeOH was added drop-wise to quench the reaction. The reaction mixture was stirred for 30 min at room temperature and then concentrated to dryness. The crude residue was suspended in MeOH, concentrated to dryness, and purified on SiO2 (40 g) using 5-10% MeOH/DCM as eluent to provide the title compound (0.32 g) as a clear oil: 1H NMR (CDCl3, 400 mHz) δ (ppm): 3.69-3.65 (m, 5H), 2.65 (m, 1H), 1.85-1.59 (m, 8H), 1.32-1.12 (m, 5H), 0.87 (m, 2H).

후처리

  1. temperaturecooled to 0° C
  2. customto quench
  3. customthe reaction
  4. stirringThe reaction mixture was stirred for 30 min at room temperature
  5. concentrationconcentrated to dryness
  6. concentrationconcentrated to dryness
  7. custompurified on SiO2 (40 g)

출처 및 근거

ORD 기록
ord-4cdb1f04afe54279b255e2b3e18cc56e
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106232B2

반응 노트

불러오는 중…