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 359567Notes

Reaction equation

HRID 359567 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])[C:9]=2/[CH:21]=[CH:22]/[CH:23]=[O:24])=[CH:4][C:3]=1[CH3:25].[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:21]=[CH:22]/[CH:23]([OH:24])[CH2:38][CH:36]([OH:37])[CH2:35][C:34]([O:40][CH3:41])=[O:39])=[CH:4][C:3]=1[CH3:25]

Participants

7

Reactant 5

HCID 7357TriethylboraneHCID 7757Methyl acetoacetateHCID 2724682Lithium diisopropylamideHCID 4311764Sodium borohydrideHCID 15056967(E)-3-{2-(4-fluoro-3-methylphenyl)-4-(pyrrolidin-1-yl)-6,6-dimethylcyclohex-1-en-1-yl}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-93c6a2aef4ef4535bc5317afd7a33edb
Source dataset
uspto-grants-1991_03
Patent number
US05001144

Reaction notes

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