N-bromobutanimide → HCID 15380074, compound

HRID 1736641Notes

Reaction equation

HRID 1736641 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C@:14]([OH:25])([CH2:15][CH:16]([OH:24])[CH2:17][CH2:18]1)[C@H:13]([OH:26])[CH2:12]3)([O:3][CH3:4])=[O:2].BrN1C(=O)CCC1=O>O1CCOCC1.O>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C@:14]([OH:25])([CH2:15][C@@H:16]([OH:24])[CH2:17][CH2:18]1)[C:13](=[O:26])[CH2:12]3)([O:3][CH3:4])=[O:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 86749671HCID 86749671, compound

Product 1

HCID 15380074HCID 15380074, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of 17β-Carbomethoxy-3,β,5α,6β-trihydroxy-androstane (43.5 g, 0.24 mol), as prepared in example 16, in 450 mL of dioxane is diluted with 50 mL of water, and maintained at 25° C. by means of an external cooling bath. To this suspension is added N-bromosuccinimide (22.5 g, 0.25 mol). The mixture is stirred for 8 h. The mixture is cooled in an ice bath and the solid collected by filtration, washed with 50% methanol/water, and air dried to afford 17β-carbomethoxy-6-oxo-3β,5α-dihydroxy-androstane as a white solid, mp 258°-260° C. Anal. Calcd. for C21H32O5 : C, 69.20; H, 8.85. Found: C, 69.38; H, 8.92.

Workup

  1. temperatureThe mixture is cooled in an ice bath
  2. filtrationthe solid collected by filtration
  3. washwashed with 50% methanol/water, and air
  4. customdried

Sources & evidence

ORD record
ord-026d7d9fb6094e29ad3c15130adea5ed
Source dataset
uspto-grants-1996_07
Patent number
US05541322

Reaction notes

Loading…