Acetic Anhydride → HCID 69134686, compound

HRID 1912680Notes

Reaction equation

HRID 1912680 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH:20]2[C@:15]([CH3:22])([CH2:16][CH2:17][C:18](=[O:21])[CH2:19]2)[C@@H:14]2[C@H:5]([C@H:6]3[C@@:10]([CH2:12][CH2:13]2)([CH3:11])[C:9](=[O:23])[CH2:8][CH2:7]3)[CH2:4]1.[CH3:24][C:25](OC(C)=O)=[O:26]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:25]([O:1][CH2:2][C@@H:3]1[CH:20]2[C@:15]([CH3:22])([CH2:16][CH2:17][C:18](=[O:21])[CH2:19]2)[C@@H:14]2[C@H:5]([C@H:6]3[C@@:10]([CH2:12][CH2:13]2)([CH3:11])[C:9](=[O:23])[CH2:8][CH2:7]3)[CH2:4]1)(=[O:26])[CH3:24]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 690108246alpha-Hydroxymethylandrostane-3,17-dione

Product 1

HCID 69134686HCID 69134686, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a stirred solution of 6α-hydroxymethylandrostane-3,17-dione (II-an, Prepn. 14, 42 mg) in pyridine (1.5 mL) at 0° C., DMAP (1 mg) and Ac2O were added. After stirring overnight at room temperature, the solution was evaporated. The residue was treated with 1N HCl and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated to dryness to give the title compound II-ao (91%). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 3.97 (m, 2H), 2.53-0.80 (m, 21H), 1.99 (m, 3H), 1.13 (s, 3H), 0.88 (s, 3H).

Workup

  1. customthe solution was evaporated
  2. additionThe residue was treated with 1N HCl
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-68e42e2694bd41b1bb895e4c700c797b
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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