Hydrochloric Acid → HCID 90388597, compound

HRID 2201749Notes

Reaction equation

HRID 2201749 reaction equation
[CH3:1][C@:2]12[C:18](=[O:19])[CH2:17][CH2:16][C@@H:15]1[CH2:14][C@H:13]1[C@@H:4]([CH2:5][CH2:6][C@H:7]3[C@@H:12]1[CH2:11][CH2:10][C:9](=[O:20])[CH2:8]3)[CH2:3]2.Cl>C1COCC1>[OH:20][CH:9]1[CH2:8][C@@H:7]2[C@@H:12]([C@@H:13]3[C@@H:4]([CH2:5][CH2:6]2)[CH2:3][C@@:2]2([CH3:1])[C:18](=[O:19])[CH2:17][CH2:16][C@@H:15]2[CH2:14]3)[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90388261HCID 90388261, compound

Product 1

HCID 90388597HCID 90388597, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 54 (110 mg, 0.4 mmol) in THF (10 mL) was added LiAl(OtBu)3H at 40° C. After 2 h, 3 N HCl, was added and the product extracted into EtOAc (50 mL×3). The combined extracts were dried, filtered and concentrated. The residue was purified by flash column chromatography (silica gel eluted with 25% EtOAc in hexanes) to give compound 55 (4aR separated from 4aS diastereomer, 65 mg, 56% from compound 36) as a white solid: mp 174-176° C.; [α]D25 −36.2 (c 0.21, CHCl3); 1H NMR (CDCl3) δ 3.65-3.55 (m, 1H), 0.82 (s, 3H); 13C NMR (CDCl3) δ 221.1, 71.4, 47.9, 45.7, 40.1, 39.1, 38.8, 38.4, 36.2, 35.6, 35.5, 31.7, 29.6, 29.3, 28.4, 25.5, 24.0, 13.5; IR νmax 3460, 1738 cm−1. Anal. Calcd for (C18H28O2): C, 78.21; H, 10.21. Found: C, 78.37; H, 10.20.

Workup

  1. extractionthe product extracted into EtOAc (50 mL×3)
  2. customThe combined extracts were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (silica gel eluted with 25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-da734b24703144ca8dc3b5877b91b4d8
Source dataset
uspto-grants-2016_06
Patent number
US09365502B2

Reaction notes

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