Borane;tetrahydrofuran → HCID 70225554, compound

HRID 1532871Notes

Reaction equation

HRID 1532871 reaction equation
[CH:1]1([CH2:7][C@H:8]([OH:12])[C:9](O)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B.C1COCC1>C1COCC1>[CH:1]1([CH2:7][C@H:8]([OH:12])[CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 12756210(S)-a-Hydroxy-cyclohexanepropanoic acid

Product 1

HCID 70225554HCID 70225554, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-3-cyclohexyllactic acid (15 g) in THF (100 mL) at 0° C. was added 1M BH3-THF (130 mL), and the reaction was warmed to ambient temperature. After 5 h, the reaction was quenched cautiously with aqueous THF (1:1, 100 mL), then with 1M KOH (100 mL). The reaction was concentrated, diluted with water (200 mL), and washed with EtOAc (3×150 mL). The organic extracts were washed with brine (100 mL), dried (MgSO4), filtered and concentrated to give a colorless oil (14 g). 1H NMR (300 MHz, CDCl3) δ0.80-1.04 (m, 2H), 1.05-2.00 (m, 13H), 3.41 (dd, J=10.8, 7.5 Hz, 1H), 3.64 (dd, J=10.8, 2.7 Hz, 1H), 3.84 (m, 1H). MS(CI/NH3) m/e: (M+NH4)+ 176.

Workup

  1. customthe reaction was quenched cautiously with aqueous THF (1:1, 100 mL)
  2. concentrationThe reaction was concentrated
  3. additiondiluted with water (200 mL)
  4. washwashed with EtOAc (3×150 mL)
  5. washThe organic extracts were washed with brine (100 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b6a1bc66b4ae44e4b7f70373cca36857
Source dataset
uspto-grants-2001_03
Patent number
US06204293B1

Reaction notes

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