Nitrogen → HCID 57164245, compound

HRID 234730Notes

Reaction equation

HRID 234730 reaction equation
[CH3:1][C:2]1([OH:39])[CH:25]=[C:24]2[C@:19]([CH3:37])([CH2:20][CH2:21][C@H:22]([O:26][Si:27]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29])[CH2:23]2)[C@@H:18]2[C@@H:3]1[C@H:4]1[C@:15]([CH3:38])([CH2:16][CH2:17]2)[C@@H:7]([C@H:8]([CH3:14])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH2:6][CH2:5]1.[CH3:40][Si](C=[N+]=[N-])(C)C.N#N>C1(C)C=CC=CC=1.CO>[OH:39][C:2]1([CH3:1])[CH:25]=[C:24]2[C@:19]([CH3:37])([CH2:20][CH2:21][C@H:22]([O:26][Si:27]([CH:28]([CH3:30])[CH3:29])([CH:31]([CH3:32])[CH3:33])[CH:34]([CH3:36])[CH3:35])[CH2:23]2)[C@@H:18]2[C@@H:3]1[C@H:4]1[C@:15]([CH3:38])([CH2:16][CH2:17]2)[C@@H:7]([C@H:8]([CH3:14])[CH2:9][CH2:10][C:11]([O:13][CH3:40])=[O:12])[CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 947NitrogenHCID 167693TrimethylsilyldiazomethaneHCID 57267156HCID 57267156, compound

Product 1

HCID 57164245HCID 57164245, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 7-hydroxy-7-methyl-3β-triisopropylsilyl-oxychol-5-en-24-oic acid (5) (5.38 g, 9.68 mmoles) in toluene (70 ml) and methanol (20 ml) was added dropwise at room temperature trimethylsilyldiazomethane (2.0N in hexane, ~5 ml). After 30 minutes N2 evolution ceased, and the reaction mixture was a pale yellow. The solvent was removed in vacuo to give 4.67 g of crude 6 as a brown syrup. NMR (CDCl3) indicated a mixture of 7-isomers: δ0.69 (two peaks, 18-Me); 3.63 (s, CO2Me); 5.12 & 5.18 (6-H). The mixture was used directly in the next reaction (Example 6).

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-2f677d0df96b485ea69bb38e78856b90
Source dataset
uspto-grants-1997_01
Patent number
US05595996

Reaction notes

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