(S)-2-((R)-2-methyl-pentyl)-succinic acid 4-tert-butyl ester → (3S,5R)-3-Hydroxymethyl-5-methyl-octanoic Acid Tert-butyl Ester

HRID 479044Notes

Reaction equation

HRID 479044 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][C@H:8]([CH2:12][C@H:13]([CH3:17])[CH2:14][CH2:15][CH3:16])[C:9](O)=[O:10])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.[Cl-].[Na+].O>[C:1]([O:5][C:6](=[O:18])[CH2:7][C@@H:8]([CH2:9][OH:10])[CH2:12][C@H:13]([CH3:17])[CH2:14][CH2:15][CH3:16])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 21031299(S)-2-((R)-2-methyl-pentyl)-succinic acid 4-tert-butyl ester

Product 1

HCID 57070108(3S,5R)-3-Hydroxymethyl-5-methyl-octanoic Acid Tert-butyl EsterYield 59%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To acid 102 (3.68 g, 0.014 mol) in THF (100 mL) at 0° C. was added BH3.Me2 (36 mL of a 2 M solution in THF, Aldrich) upon which the solution was warmed to room temperature. After 15 hours ice was carefully added (in order to control the effervescence) to the solution followed by brine. The solution was extracted with ether and the combined organic phases dried (MgSO4) and concentrated under reduced pressure. Flash chromatography (4:1 hexane/EtOAc) gave alcohol 103 as an oil (2.0 g, 59%). 13C NMR (100 MHz; CDCl3) 173.56, 80.85, 65.91, 39.74, 39.20, 38.90, 35.65, 29.99, 28.31, 20.18, 19.99, 14.56.

Workup

  1. additionAfter 15 hours ice was carefully added (in order
  2. extractionThe solution was extracted with ether
  3. dry with materialthe combined organic phases dried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b39c61dadeb3457ebe7bbb70aee0d0f9
Source dataset
uspto-grants-2003_11
Patent number
US06642398B2

Reaction notes

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