2,6-Lutidine → HCID 87737091, compound

HRID 2252485Notes

Reaction equation

HRID 2252485 reaction equation
[Si:1](OS(C(F)(F)F)(=O)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Si:16]([O:23][C@@H:24]([CH2:50][C@H:51]([OH:79])/[CH:52]=[CH:53]\[C@H:54]([CH3:78])[C@H:55]([O:70][Si:71]([C:74]([CH3:77])([CH3:76])[CH3:75])([CH3:73])[CH3:72])[C@@H:56]([CH3:69])[CH2:57][C@@H:58]([CH3:68])[CH2:59][O:60][Si:61]([C:64]([CH3:67])([CH3:66])[CH3:65])([CH3:63])[CH3:62])[C@H:25]([CH3:49])/[CH:26]=[CH:27]/[CH2:28][O:29][C:30]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].N1C(C)=CC=CC=1C>C(Cl)Cl>[Si:16]([O:23][C@@H:24]([CH2:50][C@H:51]([O:79][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])/[CH:52]=[CH:53]\[C@H:54]([CH3:78])[C@H:55]([O:70][Si:71]([C:74]([CH3:75])([CH3:76])[CH3:77])([CH3:73])[CH3:72])[C@@H:56]([CH3:69])[CH2:57][C@@H:58]([CH3:68])[CH2:59][O:60][Si:61]([C:64]([CH3:65])([CH3:66])[CH3:67])([CH3:63])[CH3:62])[C@H:25]([CH3:49])/[CH:26]=[CH:27]/[CH2:28][O:29][C:30]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)([C:19]([CH3:20])([CH3:21])[CH3:22])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 11240029HCID 11240029, compound

Product 1

HCID 87737091HCID 87737091, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

TBSOTf (2.08 mL, 9.07 mmol) was added to a stirred solution of the alcohol 34 (3.82 g, 4.11 mmol) and 2,6-lutidine (1.14 mL, 9.85 mmol) in CH2Cl2 (14 mL) at 0° C. The reaction mixture was stirred for 1 h at 0° C. The reaction mixture was quenched by the addition of H2O (25 mL). The reaction mixture was extracted with CH2Cl2 which was dried over MgSO4, filtered and the solvent was evaporated under reduced pressure. The residue was purified by short column chromatography (hexane/EtOAc 19:1) to obtain 35 (4.27 g, 99%) as a colorless oil: IR (CHCl3) 2956, 2929, 2856, 1471, 1462, 1449, 1255, 1089, 1005, 836, 773, 705 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.60 (m, 6H), 7.39 (m, 9H), 5.77 (m, 2H), 5.56 (t, J=10.8 Hz, 1H), 5.42 (dd, J=11.0, 8.2 Hz, 1H), 4.69 (m, 1H), 4.07 (m, 1H), 3.71 (d, J=3.8 Hz, 2H), 3.64 (dd, J=9.8, 4.8 Hz, 1H), 3.53 (m, 1H), 3.40 (dd, J=9.6, 7.5 Hz, 1H), 2.74 (m, 1H), 2.55 (m, 1H), 1.89 (m, 3H), 1.59 (m, 3H), 1.12 (d, J=6.2 Hz, 6H), 1.04 (m, 42H), 0.26 (s, 3H), 0.24 (s, 3H), 0.19 (s, 6H), 0.18 (s, 3H), 0.17 (s, 6H), 0.16 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 144.4, 134.5, 132.9, 132.6, 128.7, 127.7, 126.8, 86.8, 79.9, 72.3, 68.3, 66.5, 65.1, 64.1, 42.4, 41.6, 37.9, 36.0, 35.3, 33.6, 26.3, 26.02, 25.97, 25.7, 19.4, 18.5, 18.4, 18.20, 18.15, 18.1, 15.5, 13.3, −2.9, −3.5, −3.7, −4.1, −4.2, −4.3, −5.3; LRMS (ESI) 1065.9 [M+Na]+, 413.3, 359.3, 328.3, 243.1; HRMS (ESI) calcd for C62H106O5Si4Na 1065.7015 [M+Na]+, found 1065.7026; [α]20D−10.4 (c 0.53, CHCl3).

Workup

  1. customThe reaction mixture was quenched by the addition of H2O (25 mL)
  2. extractionThe reaction mixture was extracted with CH2Cl2 which
  3. dry with materialwas dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by short column chromatography (hexane/EtOAc 19:1)

Sources & evidence

ORD record
ord-d42890207ae34078aef088936b0bb8ad
Source dataset
uspto-grants-2008_01
Patent number
US07321046B2

Reaction notes

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