HCID 53923952, compound → HCID 9888409, compound

HRID 1069058Notes

Reaction equation

HRID 1069058 reaction equation
C([O:9][C@H:10]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C@@H:12]([CH2:13][CH2:14][C:15]3[C:16]4[C@:22]([CH3:30])([CH2:23][CH2:24][C:25]=32)[C:19](=[CH:20][CH3:21])[CH2:18][CH:17]=4)[C:11]1([CH3:32])[CH3:31])(=O)C1C=CC=CC=1.C([O:41][C@H:42]1[CH2:60][CH2:59][C@@:58]2(C)[C@@H:44](CCC3C4[C@](C)(CCC=32)[C@@H](C=C)CC=4)[C:43]1(C)C)(=O)C1C=CC=CC=1>>[CH3:31][C:11]1([CH3:32])[C@@H:10]([OH:9])[CH2:28][CH2:27][C@@:26]2([CH3:29])[C@H:12]1[CH2:13][CH2:14][C:15]1[C:16]3[C@:22]([CH3:30])([CH2:23][CH2:24][C:25]=12)[C@@H:19]([C@H:20]([O:41][C:42]1[CH:60]=[CH:59][CH:58]=[CH:44][CH:43]=1)[CH3:21])[CH2:18][CH:17]=3

Participants

3

Reactant 2

HCID 53923952HCID 53923952, compoundHCID 54022085HCID 54022085, compound

Product 1

HCID 9888409HCID 9888409, compound

Procedure

—1,1′-(Azodicarbonyl)dipiperidine (5.54 g) was added to an ice-cooled solution of compound 13a (2.0 g), triphenylphosphine (5.76 g), and phenol (2.06 g) in dry THF (10 ml). After 5 min. stirring dry THF (60 ml) was added and the reaction mixture was stirred for 2 h at room temperature. Then it was poured into heptane (100 ml); the resulting mixture was filtered and the filtrate was concentrated under reduced pressure. Column chromatography afforded (3β,5α,20R)4,4-dimethyl-20-phenoxypregna-8,14-dien-3-ol benzoate (compound 14b), together with the elimination products (3β,5α)-4,4-dimethylpregna-8,14,17(20)-trien-3-ol benzoate and (3β,5α)-4,4-dimethylpregna-8,14,20-trien-3-ol benzoate (2.80 g totally). The product was used in the following step without further purification.

Workup

  1. customThe product was used in the following step without further purification

Sources & evidence

ORD record
ord-72e288660ec24391afe6a54aef123b0f
Source dataset
uspto-grants-2001_06
Patent number
US06251887B1

Reaction notes

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