Sodium borohydride → 5-{3-[(1R,2R,3R,5R)-5-Chloro-2-((E)-3-hydroxy-oct-1-enyl)-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propyl}-thiophene-2-carboxylic acid methyl ester

HRID 1470679Notes

Reaction equation

HRID 1470679 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]([C:7]1[S:8][C:9]([CH2:12][CH2:13][CH2:14][C@H:15]2[C@H:19]([Cl:20])[CH2:18][C@@H:17]([O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)[C@@H:16]2/[CH:28]=[CH:29]/[C:30](=[O:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:10][CH:11]=1)=[O:6]>CO>[CH3:3][O:4][C:5]([C:7]1[S:8][C:9]([CH2:12][CH2:13][CH2:14][C@H:15]2[C@H:19]([Cl:20])[CH2:18][C@@H:17]([O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)[C@@H:16]2/[CH:28]=[CH:29]/[CH:30]([OH:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:10][CH:11]=1)=[O:6]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57692812HCID 57692812, compound

Product 1

HCID 576928175-{3-[(1R,2R,3R,5R)-5-Chloro-2-((E)-3-hydroxy-oct-1-enyl)-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-propyl}-thiophene-2-carboxylic acid methyl esterYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (9.2 mg, 0.24 mmol) was added to a solution of ketone 4-3 (59 mg, 0.12 mmol) in methanol (1 mL). The reaction was stirred at room temperature for 2 h and then was quenched by addition of 5 mL 1 M HCl. The resulting mixture was extracted with CH2Cl2 and the combined CH2Cl2 solution was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (ethyl acetate/hexanes) gave the title compound (48 mg, 80%).

Workup

  1. customwas quenched by addition of 5 mL 1 M HCl
  2. extractionThe resulting mixture was extracted with CH2Cl2
  3. dry with materialthe combined CH2Cl2 solution was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography on silica gel (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b13754997529450eb8e18adff6dffba1
Source dataset
uspto-grants-2015_04
Patent number
US09006464B2

Reaction notes

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