Chloroform → (3R,5S)-5-(((tert-Butyldimethylsilyl)oxy)methyl)pyrrolidin-3-ol

HRID 1830942노트

반응식

HRID 1830942 반응식
C(OC([N:11]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:12]1[CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])=O)C1C=CC=CC=1.C(Cl)(Cl)Cl.C(OC(N1C[C@H](O)C[C@H]1C(OC)=O)=O)C=C>C(OCC)(=O)C.C(O)C.[Pd]>[Si:19]([O:18][CH2:17][C@@H:12]1[CH2:13][C@@H:14]([OH:16])[CH2:15][NH:11]1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

참가 물질

7

반응물 3

HCID 6212ChloroformHCID 10633157(2S,4R)-1-allyloxycarbonyl-2-methoxycarbonyl-4-hydroxypyrrolidineHCID 57280098benzyl (2S,4R)-2-{[(tert-butyldimethylsilyl)oxy]methyl}-4-hydroxypyrrolidine-1-carboxylate

생성물 1

HCID 11481662(3R,5S)-5-(((tert-Butyldimethylsilyl)oxy)methyl)pyrrolidin-3-ol

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

A slurry of 10% Pd/C (190 mg) in ethyl acetate (20 mL) was added to a solution of TBDMS ether (48) (1.90 g, 5.19 mmol) in ethanol (100 mL). The reaction mixture was hydrogenated (Parr apparatus) for 16 h. The catalyst was removed by vacuum filtration through Celite and excess solvent was evaporated under reduced pressure to give a yellow oil in quantitative yield (1.20 g, 100%). [α]22D=+35.6° (c 0.042, CHCl3). 1H NMR (CDCl3): δ-(0.07-0.08) (m, 6H, H1′, H2′), 0.82 (s, 9H, H3′, H4′, H5′), 1.68-1.73 (m, 2H, H1,), 2.99-3.11 (m, 2H, H11), 3.47-3.50 (m, 3H, H11a, H3), 4.09 (bs, 1H, NH or OH), 4.32 (bs, 1H, NH or OH). 13C NMR (CDCl3): δ−5.4 (C3′, C5′, C6′), 18.1 (C4′), 25.8 (C1′, C2′), 37.4 (C1), 54.6 (C11), 58.1 (C2), 64.6 (C3), 72.2 (C11a). IR (thin film): ν=3330 (OH), 2928, 2857, 1557, 1421, 1331 (C—CH3), 1249 (CH3—Si), 1204 (t-Bu), 1191 (t-Bu), 1100 (Si—O), 1073, 993, 713 cm−1. MS (CI) m/e (relative intensity): 232 (M+., 100), 230 (13), 174 (5), 133 (6), 86 (6).

후처리

  1. customfor 16 h
  2. customThe catalyst was removed by vacuum filtration through Celite and excess solvent
  3. customwas evaporated under reduced pressure
  4. customto give a yellow oil in quantitative yield (1.20 g, 100%)

출처 및 근거

ORD 기록
ord-df308c8b59f34f93bc2d3d613d2244dc
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067511B2

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