HCID 67924099, compound → HCID 67924059, compound

HRID 1493661Notes

Reaction equation

HRID 1493661 reaction equation
C([O:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:12]([CH2:13][CH2:14][C:15]3[C@@:16]4([CH2:37][C:38]([O:40]CC)=[O:39])[C@:28]([CH3:36])([CH2:29][CH2:30][C:31]=32)[C@@H:19]([C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH:18]=[CH:17]4)[CH2:11]1)(=O)C1C=CC=CC=1>COCCOCCOC.[OH-].[Li+]>[C:38]([CH2:37][C@:16]12[C:15]3[CH2:14][CH2:13][C@@H:12]4[C@:32]([CH3:35])([CH2:33][CH2:34][C@H:10]([OH:9])[CH2:11]4)[C:31]=3[CH2:30][CH2:29][C@:28]1([CH3:36])[C@@H:19]([C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH:18]=[CH:17]2)([OH:40])=[O:39]

Participants

4

Reactant 1

HCID 67924099HCID 67924099, compound

Product 1

HCID 67924059HCID 67924059, compound

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 8150DiglymeSolvent

Procedure

A mixture of 3β-benzoyloxy-14α-carbethoxymethyl-5α-cholest-8,15-diene (209 mg, 0.36 mmole) in diglyme (5 mL) and 1N lithium hydroxide (5 mL) was heated at 125° C. to 135° C. for 4 hours, and worked up according to the procedure described in Example 2(iii) to provide 122 mg (77%) of white, crystalline 14α-carboxymethyl-5α-cholest-8,15-dien-3β-ol; mp 221°-222° C. (from CH3CN).

Workup

  1. temperaturewas heated at 125° C. to 135° C. for 4 hours

Sources & evidence

ORD record
ord-3ce0e97e9c9f49a3a1603502562c1b51
Source dataset
uspto-grants-1991_06
Patent number
US05023250

Reaction notes

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