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 654544Notes

Reaction equation

HRID 654544 reaction equation
[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]

Participants

7

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-85874b406056472ca6300235678a06c6
Source dataset
uspto-grants-1992_07
Patent number
US05132312

Reaction notes

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