Boron trifluoride etherate → (2S,4R)-4-tert-butoxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid benzyl ester

HRID 458366노트

반응식

HRID 458366 반응식
[CH2:1]([O:8][C:9]([C@@H:11]1[CH2:15][C@@H:14]([OH:16])[CH2:13][N:12]1[S:17]([C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)(=[O:19])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(F)(F)F.CCOCC.[CH3:39][C:40](=[CH2:42])[CH3:41].C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:8][C:9]([C@@H:11]1[CH2:15][C@@H:14]([O:16][C:40]([CH3:42])([CH3:41])[CH3:39])[CH2:13][N:12]1[S:17]([C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)(=[O:19])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 8000Boron trifluoride etherateHCID 8255IsobutyleneHCID 516892Sodium BicarbonateHCID 69430249(2S,4R)-4-hydroxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid benzyl ester

생성물 1

HCID 69433308(2S,4R)-4-tert-butoxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid benzyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-20 °C

실험 절차

Tert-Butyletherification: To a solution of (2S,4R)-4-hydroxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid benzyl ester (14.8 g) in dichloromethane (140 ml) were added boron trifluoride ethyl etherate (3 ml) and isobutylene (cooled and liquefied at −30° C., 170 ml) at −30° C. The turbid reaction mixture was stirred at −20° C. for 2 h, poured onto a saturated sodium bicarbonate solution, and extracted with dichloromethane. The organic phases were washed with water, dried over magnesium sulphate and concentrated. The residue was chromatographed on silica gel using EtOAc/hexane 1:4 and 1:2 as eluents to obtain (2S,4R)-4-tert-butoxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid benzyl ester (16.4 g) as a glassy syrup, MS: 467 (M).

후처리

  1. customThe turbid reaction mixture
  2. extractionextracted with dichloromethane
  3. washThe organic phases were washed with water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-429175fa4f3f4315a15d7d05b99f0684
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189756B2

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