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

HRID 1830942Notes

Reaction equation

HRID 1830942 reaction equation
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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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%)

Sources & evidence

ORD record
ord-df308c8b59f34f93bc2d3d613d2244dc
Source dataset
uspto-grants-2006_06
Patent number
US07067511B2

Reaction notes

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