Ethyl Acetate → Methyl 1-(((1(R)-(3-(2-(3-chlorothieno[3,2-b]pyridin-5-yl)-ethyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropaneacetate

HRID 2259500Notes

Reaction equation

HRID 2259500 reaction equation
[Cl:1][C:2]1[C:6]2=[N:7][C:8]([CH:11]=[CH:12][C:13]3[CH:14]=[C:15]([C@H:19]([S:32][CH2:33][C:34]4([CH2:37][C:38]([O:40][CH3:41])=[O:39])[CH2:36][CH2:35]4)[CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:28]([OH:31])([CH3:30])[CH3:29])[CH:16]=[CH:17][CH:18]=3)=[CH:9][CH:10]=[C:5]2[S:4][CH:3]=1.CCOC(C)=O>C1COCC1>[Cl:1][C:2]1[C:6]2=[N:7][C:8]([CH2:11][CH2:12][C:13]3[CH:14]=[C:15]([C@H:19]([S:32][CH2:33][C:34]4([CH2:37][C:38]([O:40][CH3:41])=[O:39])[CH2:36][CH2:35]4)[CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:28]([OH:31])([CH3:30])[CH3:29])[CH:16]=[CH:17][CH:18]=3)=[CH:9][CH:10]=[C:5]2[S:4][CH:3]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 53750405Methyl 1-(((1(R)-(3-(2-(3-chlorothieno[3,2-b]pyridin-5-yl)-ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)-thio)methyl)cyclopropaneacetate

Product 1

HCID 22857738Methyl 1-(((1(R)-(3-(2-(3-chlorothieno[3,2-b]pyridin-5-yl)-ethyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropaneacetateYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the olefin of Step 18 of Example 1 (270 mg, 0.456 mmol) in THF at 0° C. was added BH3 in THF (1M) (1.36 mL, 1.37 mmol). The mixture was stirred for 5 hr. at room temperature. Addition of 25% aq. NH4OAc and extraction with EtOAc followed by purification by flash chromatography (15% EtOAc in toluene) afforded 110 mg (41%)of the saturated compound.

Workup

  1. customat room temperature
  2. customfollowed by purification by flash chromatography (15% EtOAc in toluene)

Sources & evidence

ORD record
ord-c74db3427e504c1c9f9a6dda3cbccfe6
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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