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Sodium Carbonate → (3R,3aR,6S,6aS)-(9H-fluoren-9-yl)methyl 3-hydroxy-6-(methylthio)tetrahydro-2H-furo[3,2-b]pyrrole-4(5H)-carboxylate

HRID 1716462
Notes
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Reaction equation

HRID 1716462 reaction equation
[CH3:1][S:2][C@H:3]1[CH2:7][NH:6][C@@H:5]2[C@@H:8]([OH:11])[CH2:9][O:10][C@H:4]12.C(=O)([O-])[O-].[Na+].[Na+].[CH:18]1[C:30]2[CH:29]([CH2:31][O:32][C:33](Cl)=[O:34])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]=2[CH:21]=[CH:20][CH:19]=1>O1CCOCC1.O>[OH:11][C@@H:8]1[C@H:5]2[N:6]([C:33]([O:32][CH2:31][CH:29]3[C:28]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:22]4[C:30]3=[CH:18][CH:19]=[CH:20][CH:21]=4)=[O:34])[CH2:7][C@H:3]([S:2][CH3:1])[C@H:4]2[O:10][CH2:9]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 343679-Fluorenylmethyl chloroformateHCID 67442415HCID 67442415, compound

Product 1

HCID 67441663(3R,3aR,6S,6aS)-(9H-fluoren-9-yl)methyl 3-hydroxy-6-(methylthio)tetrahydro-2H-furo[3,2-b]pyrrole-4(5H)-carboxylateYield 60%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
2×
HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of (3R,3aR,6S,6aS)-6-(methylthio)hexahydro-2H-furo[3,2-b]pyrrol-3-ol in 1,4-dioxane (5 mL) was added whilst stirring to a solution of sodium carbonate (123 mg, 1.16 mmol) in water (1.5 mL) at 0° C. A solution of 9-fluorenylmethoxycarbonyl chloride (150 mg, 0.58 mmol) in 1,4-dioxane (1.5 mL) was added dropwise over 5 minutes then the mixture allowed to warm to ambient temperature over 2 hours. Water (20 mL) was added and the product extracted into dichloromethane (3×10 mL). The organic layer was dried (Na2SO4), filtered and reduced in vacuo to leave a residue. Flash chromatography over silica, eluting with diethyl ether:pentane mixtures 2:1 gave alcohol (55) as a white solid (130 mg, 60%). TLC (Rf=0.19, Et2O:pentane 2:1); HPLC-MS 398.2 [M+H]+, 420.1 [M+Na]+, 817.3 [2M+H]+; analytical HPLC single main peak, Rt=16.096 min., [□]D17−59.4° (c=2.78, CHCl3); δH (500 MHz, CDCl3) mixture of rotamers major:minor 4:3; 1.06 (0.57H, d, J=3.63 Hz, OH major), 2.04 (1.71H, s, SCH3 major), 2.14 (1.29H, s, SCH3 minor), 2.57 (0.43H, d, J=2.83 Hz, OH minor), 3.10 (0.57H, d, J=5.40 Hz, FmocNCH2 major), 3.21-3.24 (0.43H, m, FmocNCH2 minor), 3.41 (0.57H, dd, 5.57 Hz, OCH2CHOH major), 3.52-3.82 (4.43H, m, FmocNCH, CHSCH3 OCH2CHOH minor, 1×FmocNCH2 and 1×OCH2CHOH), 3.92 (0.43H, dd, 4.41 Hz, OCH2CHOH minor), 4.23-4.84 (4.57H, m, Fmoc CH, OCHCHSCH3, Fmoc CH2 minor and 1×OCH2CHOH major), 7.28-7.80 (8H, Fmoc aromatic CH); δC (125 MHz, CDCl3) 14.574/14.768 (SCH3), 47.234, 47.445, 48.069 and 48.826 (Fmoc CH and CHSCH3), 50.417/50.633 (FmocNCH2), 65.752/67.282 (Fmoc CH2), 68.555/69.282 (FmocNCH), 74.361/74.600 (OCH2CHOH), 75.774/76.148 (OCH2CHOH), 85.505/86.026 (OCHCHOCH3), 119.848, 120.003, 120.029, 124.512, 124.593, 124.946, 127.030, 127.063, 127.427, 127.507, 127.755, 127.771 and 127.892 (Fmoc aromatic CH), 141.196, 141.320, 141.378, 141.428, 143.581, 143.818, 143.890 and 143.964 (Fmoc quaternary), 154.115/154.849 (Fmoc C═O).

Workup

  1. extractionthe product extracted into dichloromethane (3×10 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customto leave a residue
  5. washFlash chromatography over silica, eluting with diethyl ether

Sources & evidence

ORD record
ord-d2f0ae034bd749aa9d487ea508158e87
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07803803B2

Reaction notes

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