1,3-Dibromo-5,5-dimethylhydantoin → HCID 69306767, compound

HRID 895849Notes

Reaction equation

HRID 895849 reaction equation
[C:1]([O:9][C@H:10]1[CH2:40][CH2:39][C@@:38]2([CH3:41])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:37]2[CH2:36][CH2:35][C@@:34]2([CH3:42])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@@H:20]([CH2:22][O:23][Si:24]([CH:31]([CH3:33])[CH3:32])([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])[CH3:21])[C:11]1([CH3:44])[CH3:43])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrN1C(C)(C)C(=O)N(Br)C1=O.CC1C=C(C)C=C(C)N=1>>[C:1]([O:9][C@H:10]1[CH2:40][CH2:39][C@@:38]2([CH3:41])[C:12](=[CH:13][CH:14]=[C:15]3[C@@H:37]2[CH2:36][CH2:35][C@@:34]2([CH3:42])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@@H:20]([CH2:22][O:23][Si:24]([CH:31]([CH3:32])[CH3:33])([CH:25]([CH3:26])[CH3:27])[CH:28]([CH3:30])[CH3:29])[CH3:21])[C:11]1([CH3:44])[CH3:43])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 79532,4,6-TrimethylpyridineHCID 11285024HCID 11285024, compound

Product 1

HCID 69306767HCID 69306767, compoundYield 100.1%

Procedure

42 g of (20S)-4,4-dimethyl-20-[((triisopropylsilyl)oxy)methyl]-pregna-5-en-3β-ol benzoate were treated with 13.7 g 1,3-dibrom-5,5-dimethyl-hydantoin and 18 ml 2,4,6-trimethylpyridine as described in Example 1e) to give (without purification by column chromatography) 41.9 g of (20S)-4,4-dimethyl-20-[((triisopropylsilyl)oxy)methyl]-pregna-5,7-dien-3β-ol benzoate.

Sources & evidence

ORD record
ord-bf7064a6b5e7451fb25ae9c270f1478e
Source dataset
uspto-grants-2005_07
Patent number
US06916921B2

Reaction notes

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