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 654544노트

반응식

HRID 654544 반응식
[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]

참가 물질

7

반응물 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

생성물 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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-85874b406056472ca6300235678a06c6
출처 데이터셋
uspto-grants-1992_07
특허 번호
US05132312

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