Triethylamine → Trans-(E)-6-{2-{2-(4-fluoro-3-methylphenyl)-4-(pyrrolidin-1-yl)-6,6-dimethylcyclohex-1-en-1-yl}ethenyl}-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one

HRID 359568Notes

Reaction equation

HRID 359568 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]([OH:32])[CH2:24][CH:25]([OH:31])[CH2:26][C:27]([O:29]C)=O)=[CH:4][C:3]=1[CH3:33].[OH-].[Na+].ClC(OCC)=O.CCN(CC)CC>CO.C(Cl)Cl.O>[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]([CH3:19])([CH3:20])[C:9]=2/[CH:21]=[CH:22]/[C@@H:23]2[O:32][C:27](=[O:29])[CH2:26][C@@H:25]([OH:31])[CH2:24]2)=[CH:4][C:3]=1[CH3:33]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 86744089Methyl (E)-7-{2-(4-fluoro-3-methylphenyl)-4-(pyrrolidin-1-yl)-6,6-dimethylcyclohex-1-en-1-yl}-3,5-dihydroxyhept-6-enoate

Product 1

HCID 86744090Trans-(E)-6-{2-{2-(4-fluoro-3-methylphenyl)-4-(pyrrolidin-1-yl)-6,6-dimethylcyclohex-1-en-1-yl}ethenyl}-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In a manner similar to Scheme I, 34 (0.19 g) was treated with 2N NaOH in methanol at 0°-5° C. for 18 h, followed by ethyl chloroformate (0.254 mmol) and Et3N in CH2Cl2 at 0°-5° C. Workup and purification of the residue by SiO2 using 1% Et3N in EtOAc as eluent yielded the product. mp 120°-3° C. Anal. C26H34FNO3. 0.5 H2O: Theory C: 71.53; H: 8.08; N: 3.21; Found C.: 71.60; H: 8.17; N: 3.03.

Workup

  1. customWorkup and purification of the residue by SiO2 using 1% Et3N in EtOAc as eluent
  2. customyielded the product

Sources & evidence

ORD record
ord-783ab6075147499ab4738472f6fab39f
Source dataset
uspto-grants-1991_03
Patent number
US05001144

Reaction notes

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