Triethylamine → (1S,3R)-methanesulfonic acid 3-tert-butyldimethylsilyloxy-cyclopentyl ester

HRID 2562노트

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HRID 2562 반응식
[Si:1]([O:8][C@@H:9]1[CH2:13][CH2:12][C@H:11]([OH:14])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:15][S:16](Cl)(=[O:18])=[O:17].C(N(CC)CC)C>COC(C)(C)C>[Si:1]([O:8][C@@H:9]1[CH2:13][CH2:12][C@H:11]([O:14][S:16]([CH3:15])(=[O:18])=[O:17])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54118351(1S,3R)-3-{[tert-Butyl(dimethyl)silyl]oxy}cyclopentan-1-ol

생성물 1

HCID 54256983(1S,3R)-methanesulfonic acid 3-tert-butyldimethylsilyloxy-cyclopentyl ester수율 97%

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매

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온도
-5 °C

실험 절차

Dissolve (-)-cis-3-tert-butyldimethylsilyloxy-cyclopentanol (9.20 g, 42.5 mmol) in anhydrous tert-butyl methyl ether (50 mL) and cool to -5° C. Treat the solution with methanesulfonyl chloride (3.6 g, 46.5 mmol, mesyl chloride), followed by triethylamine (7.2 mL, 51.7 mmol), at such a rate as to keep the temperature between -5° C. and -2° C. with an ice bath. The ice bath is removed and the solution is stirred for 2 hours. The mixture is then transferred to a separatory funnel and treated with brine/water (50 mL/50 mL). The layers are separated and the aqueous layer is extracted with tert-butyl methyl ether (2×50 mL). The organic layer and extracts are combined, washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to provide the title compound (12.1 g, 97% yield) as a colorless oil; 1 H NMR (CDCl3) δ5.1 (m, 1H), 4.2 (m, 1H), 2.99 (s, 3H), 2.3 (m, 1H), 2.0 (m, 3H), 1.8 (m, 2H), 0.88 (s, 9H), 0.05 (s, 6H).

후처리

  1. customthe temperature between -5° C. and -2° C.
  2. customThe ice bath is removed
  3. customThe mixture is then transferred to a separatory funnel
  4. additiontreated with brine/water (50 mL/50 mL)
  5. customThe layers are separated
  6. extractionthe aqueous layer is extracted with tert-butyl methyl ether (2×50 mL)
  7. washwashed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-61afa5168bfe4df280f2c9386fbd28fe
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728899

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