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Triethylamine → (4R,6R)-6-{2-[(1S,2S,6S,8S,8aR)-1,2,6,7,8,8a-Hexahydro-6-t-butyldimethylsilyloxy-8-(2,2-diethylbutyryloxy)-2-methyl-1-naphthyl]ethyl}tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one

HRID 2399966
ノート
印刷プレビュー

反応式

HRID 2399966 の反応式
[CH2:1]([C:3]([CH2:9][CH3:10])([CH2:7][CH3:8])[C:4](Cl)=[O:5])[CH3:2].[Si:11]([O:18][C@H:19]1[CH2:28][C@H:27]([OH:29])[C@H:26]2[C:21]([CH:22]=[CH:23][C@H:24]([CH3:47])[C@@H:25]2[CH2:30][CH2:31][C@H:32]2[O:37][C:36](=[O:38])[CH2:35][C@H:34]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[CH2:33]2)=[CH:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1(C2C=CN=CC=2)CCCC1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Si:11]([O:18][C@H:19]1[CH2:28][C@H:27]([O:29][C:4](=[O:5])[C:3]([CH2:9][CH3:10])([CH2:7][CH3:8])[CH2:1][CH3:2])[C@H:26]2[C:21]([CH:22]=[CH:23][C@H:24]([CH3:47])[C@@H:25]2[CH2:30][CH2:31][C@H:32]2[O:37][C:36](=[O:38])[CH2:35][C@H:34]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:41])[CH3:42])[CH2:33]2)=[CH:20]1)([C:14]([CH3:15])([CH3:16])[CH3:17])([CH3:13])[CH3:12]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8471TriethylamineHCID 755674-PyrrolidinopyridineHCID 50970172,2-diethylbutanoyl ChlorideHCID 14600906Pravastatin Diol Lactone Di-(tert-butyldimethylsilyl) Ether

生成物 1

HCID 22856156(4R,6R)-6-{2-[(1S,2S,6S,8S,8aR)-1,2,6,7,8,8a-Hexahydro-6-t-butyldimethylsilyloxy-8-(2,2-diethylbutyryloxy)-2-methyl-1-naphthyl]ethyl}tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one
収率 89.4%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

1.48 g (9.1 mmol) of 2,2-diethylbutyryl chloride were added to a solution of 1.0 g (1.8 mmol) of (4R,6R)-6-{2-[(1S,2S,6S,8S,8aR)-1,2,6,7,8,8a-hexahydro-6-t-butyldimethylsilyloxy-8-hydroxy-2-methyl-1-naphthyl]ethyl}tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one [prepared as described in Example B, above] 1.67 g (11.3 mmol) of 4-(1-pyrrolidinyl)pyridine and 1.0 ml (7.1 mmol) of triethylamine in 10 ml of toluene, and the resulting mixture was heated under reflux for 10 hours. At the end of this time the reaction mixture was worked-up following a procedure similar to that described in Example 5, above, to give 1.09 g (89% yield) of the title compound.

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 10 hours

出典と根拠

ORDレコード
ord-9ecc32e69c3d4334ba29e98dbf964e9b
出典データセット
uspto-grants-1995_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05451688

反応ノート

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