HCID 70133450, compound → HCID 11336137, compound

HRID 2227239Notes

Reaction equation

HRID 2227239 reaction equation
[F:1]/[C:2](=[C:4]1\[CH2:5][CH2:6][C@@H:7]2[C@:21]\1([CH3:22])[CH2:20][CH2:19][C@H:18]1[C@H:8]2[CH2:9][CH:10]=[C:11]2[C@:16]1([CH3:17])[CH2:15][CH2:14][C@H:13]([OH:23])[CH2:12]2)/[CH3:3].CC([Si](C)(C)O[C@H]1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CC/C/2=C(\F)/C)C1)(C)C>>[F:1]/[C:2](=[C:4]1/[CH2:5][CH2:6][C@@H:7]2[C@:21]/1([CH3:22])[CH2:20][CH2:19][C@H:18]1[C@H:8]2[CH2:9][CH:10]=[C:11]2[C@:16]1([CH3:17])[CH2:15][CH2:14][C@H:13]([OH:23])[CH2:12]2)/[CH3:3]

Participants

3

Reactant 2

HCID 70133450HCID 70133450, compoundHCID 70134444HCID 70134444, compound

Product 1

HCID 11336137HCID 11336137, compound

Procedure

Prepare A11 from A10 in a manner analogous to the preparation of A8 from A7 to give A11 (204 mg, 64%) as a white crystalline solid, after crystallization from methanol: mp 153-155° C. TLC Rf 0.27, ethyl acetate/hexane (1:3); 1H NMR δ 5.37-5.33 (m, 1H), 3.59-3.46 (m, 1H), 3.49 (s, 0.6H, MeOH solvate), 179 (dt, 3H, J=17.2, 1.4 Hz, 21-Me), 1.02 (s, 3H, 19-Me), 0.89 (s, 3H,); 19F NMR δ −110.27 (q of q, J=17.2, 2.0 Hz); MS (CI, CH4) m/z (rel intensity) 319 (MH+, 7), 318 (15), 317 (28), 301 (100), 299 (39), 281 (8). Analysis. Calculated for C21H31OF. 0.2 MeOH: C, 78.38; H, 9.87. Found: C, 78.40; H, 9.82.

Workup

  1. customPrepare A11 from A10 in a manner
  2. customto give A11 (204 mg, 64%) as a white crystalline solid
  3. customafter crystallization from methanol

Sources & evidence

ORD record
ord-72ddde8ea4de4a8b975b1b07a6bdb43a
Source dataset
uspto-grants-2002_07
Patent number
US06413951B2

Reaction notes

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