Triethylborane → Methyl (E)-7-{2-(4-fluoro-3-methylphenyl)-4-(pyrrolidin-1-yl)-6,6-dimethylcyclohex-1-en-1-yl}-3,5-dihydroxyhept-6-enoate

HRID 654544ノート

反応式

HRID 654544 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH:12]([N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:11][C:10]([CH3:20])([CH3:19])[CH:9]=2)=[CH:4][C:3]=1[CH3:21].[C:22](=[O:25])=[CH:23][CH3:24].[Li+].CC([N-]C(C)C)C.[C:34]([O:40][CH3:41])(=[O:39])[CH2:35][C:36]([CH3:38])=[O:37].C(B(CC)CC)C.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH:12]([N:14]3[CH2:15][CH2:16][CH2:17][CH2:18]3)[CH2:11][C:10]([CH3:19])([CH3:20])[C:9]=2/[CH:24]=[CH:23]/[CH:22]([OH:25])[CH2:38][CH:36]([OH:37])[CH2:35][C:34]([O:40][CH3:41])=[O:39])=[CH:4][C:3]=1[CH3:21]

参加物

7

反応物 5

HCID 7357TriethylboraneHCID 7757Methyl acetoacetateHCID 2724682Lithium diisopropylamideHCID 4311764Sodium borohydrideHCID 867460012-(4-Fluoro-3-methylphenyl)-4-(pyrrolidin-1-yl)-6,6-dimethylcyclohex-1-en 1-propenal

生成物 1

HCID 86744089Methyl (E)-7-{2-(4-fluoro-3-methylphenyl)-4-(pyrrolidin-1-yl)-6,6-dimethylcyclohex-1-en-1-yl}-3,5-dihydroxyhept-6-enoate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

In a manner similar to Scheme I, 33 (2.27 g, 6,65 mmol) was treated with the LDA derived anion of methyl acetoacetate (7.98 mmol) followed by triethylborane, methanol, and NaBH4. Workup and purification by HPLC using 1% Et3N in EtOAc as eluent provided the oily product.

後処理

  1. customWorkup and purification by HPLC
  2. customprovided the oily product

出典と根拠

ORDレコード
ord-85874b406056472ca6300235678a06c6
出典データセット
uspto-grants-1992_07
特許番号
US05132312

反応ノート

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